Skip to main content
SpringerLink
Log in

Hetero Diels-Alder reactions in organic chemistry

  • Chapter
  • First Online:
Stereoselective Heterocyclic Synthesis I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 189))

Abstract

The hetero Diels-Alder reaction is one of the most important methods for the synthesis of heterocycles. In this article an overview is given for the period since 1989 describing the reaction of heterobutadienes such as oxabutadienes, thiabutadienes, azabutadienes, diaazabutadienes, nitroso-alkenes and nitroalkenes as well as of heterodienophiles such as carbonyls, thiocarbonyls, imines, iminium salts, azo- and nitroso compounds. In addition, several other less common hetero Diels-Alder reactions such as cycloadditions of thiaazabutadienes, oxaazabutadienes, dioxabutadienes, dithiabutadienes, oxathiabutadienes, diazaoxabutadienes as well as the use of N-sulfinyl-phosphaalkynes and other dienophiles are mentioned. A main point of discussion is the stereoselectivity of the reactions and the preparation of enantiopure compounds either using dienes and dienophiles carrying a chiral auxiliary or employing chiral Lewis acids. A point stressed is the synthesis of natural products using hetero Diels-Alder reactions leading to carbohydrates, alkaloids, terpenes, antibiotics, mycotoxins, cytochalasans, antitumor agents and several other classes of natural products.

Another topic is the use of high pressure in hetero Diels-Alder reactions discussing the influence on the rate constants and the stereoselectivity. Finally, modern developments such as reactions on solid phase, the use of catalytic monoclonal antibodies, transformations in aqueous solution and the microwave activation are described.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

Ac:

acetyl

AIBN:

2,2′-azobisisobutyronitrile

ATP:

aluminium tris(2,6-diphenylphenoxide)

9-BBN:

9-borabicyclo[3.3.1]nonane

BF3 · OEt2 :

boron trifluoride — diethyl ether complex

BINOL:

β-binaphthol

Bn:

benzyl

Boc:

tert-butoxycarbonyl

Bz:

benzoyl

CAN:

ammonium cerium(IV) nitrate

Cbz:

benzyloxycarbonyl

CSA:

camphorsulfonic acid

DABCO:

1,4-diazabicyclo[2.2.2]octane

DAGOH:

diacetone glucose

Danishefsky’s diene:

1-methoxy-3-trimethylsilyloxy-1,3-butadiene

DBN:

1,5-diazobicyclo[4.3.0]non-5-ene

DBPO:

dibenzoyl peroxide

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

DCC:

dicyclohexylcarbodiimide

DDQ:

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DEAD:

diethyl azodicarboxylate

DET:

diethyl tartrate

DIBAL-H:

diisobutylaluminium hydride

DIPT:

diisopropyl tartrate

DMAP:

N,N-dimethylaminopyridine

DMB:

3,4-dimethoxybenzyl

DME:

1,2-dimethoxyethane

DMF:

dimethylformamide

DMPU:

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone

DMSO:

dimethyl sulfoxide

EDDA:

ethylene diammonium diacetate

Eu(dppm)3 :

di(perfluoro-2-propoxypropionyl)methanato europium

Eu(fod)3 :

6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato europium

Eu(hfbc)3 :

3-(heptafluorobutyryl)-(+)-campherato europium

Eu(hfc)3 :

3-(heptafluoropropylhydroxymethylene)-(+)-campherato europium

Fmoc:

9-fluorenylmethoxycarbonyl

HMPA:

hexamethylphosphoric triamide

Ipc:

isopinocamphenyl

KHMDS:

potassium hexamethyldisilazanide

LDA:

lithium diisopropylamide

MCPBA:

3-chloroperoxybenzoic acid

MEM:

(2-methoxyethoxy)methyl

Mes:

mesityl

MOM:

methoxymethyl

MS:

molecular sieves

NBS:

N-bromosuccinimide

NCS:

N-chlorosuccinimide

NIS:

N-iodosuccinimide

(+)-NLE:

positive non linear effect

PCC:

pyridinium chlorochromate

PDC:

pyridinium dichromate

Ph3P:

triphenylphosphane

Pht:

phthaloyl

PMB:

4-methoxyphenyl

PNB:

4-nitrobenzyl

Pv:

pivaloyl

py:

pyridine

Red-Al:

sodium bis(2-methoxyethoxy)aluminium hydride

SEM:

2-(trimethylsilyl)ethoxymethyl

TBAF:

tetrabutylammonium fluoride

TBDMS:

tert-butyldimethylsilyl

TBDMSCl:

tert-butyldimethylsilyl chloride

TBDMSOTf:

tert-butyldimethylsilyl triflate

TBDPS:

tert-butyldiphenylsilyl

Tf:

trifluoromethanesulfonyl

thexyl:

1,1,2-trimethylpropyl

THF:

tetrahydrofuran

THP:

tetrahydropyran-2-yl

TIPDS:

1,1,3,3-tetraisopropyldisiloxane-1,3-diyl

TIPS:

triisopropylsilyl

TMEDA:

N,N,N′,N′-tetramethylethylenediamine

TMS:

trimethylsilyl

TMSBr:

trimethylsilyl bromide

TMSCl:

trimethylsilyl chloride

TMSI:

trimethylsilyl iodide

TMSOTf:

trimethylsilyl triflate

Tol:

4-methylphenyl

Ts:

4-toluenesulfonyl

References

  1. Diels O, Alder L (1928) Liebigs Ann Chem 460:98

    Article  CAS  Google Scholar 

  2. Hudlicky T (1996) Chem Rev 96:3

    Article  CAS  Google Scholar 

  3. Tietze LF, Beifuss U (1993) Angew Chem 105:137; Angew Chem Int Ed Engl 32:131

    Article  CAS  Google Scholar 

  4. Tietze LF (1996) Chem Rev 96:115

    Article  CAS  Google Scholar 

  5. Denmark SE, Thorarensen A (1996) Chem Rev 96:137

    Article  CAS  Google Scholar 

  6. Parsons PJ, Penkett CS, Shell AJ (1996) Chem Rev 96:195

    Article  CAS  Google Scholar 

  7. Waldmann H (1994) Synthesis 535

    Google Scholar 

  8. Streith J, Defoin A (1994) Synthesis 1107

    Google Scholar 

  9. Barluenga J, Tomas M (1993) Adv. Heterocycl Chem 57:1

    CAS  Google Scholar 

  10. Weinreb SM (1991) In: Trost BM (ed) Comprehensive organic synthesis. Pergamon, Oxford, vol 5, p 401–449

    Google Scholar 

  11. Boger DL (1991) In: Trost BM (ed) Comprehensive organic synthesis. Pergamon, Oxford, vol 5, p 451–512

    Google Scholar 

  12. Tietze LF (1990) J Heterocyclic Chem 27:47

    CAS  Google Scholar 

  13. Weinreb SM, Scola PM (1989) Chem Rev 89: 1525

    Article  CAS  Google Scholar 

  14. Boger DL, Weinreb SM (1987) Hetero-Diels-Alder methodology in organic synthesis. Academic Press, San Diego

    Google Scholar 

  15. Kametani T, Hibino S, (1987) In: Advances in Heterocyclic Chemistry 42:245–333

    CAS  Google Scholar 

  16. Danishefsky SJ, De Ninno MP (1987) Angew Chem 99:15; Angew Chem Int Ed Engl 26:15

    Article  CAS  Google Scholar 

  17. Schmidt RR (1986) Acc Chem Res 19:250

    Article  CAS  Google Scholar 

  18. Boger DL (1986) Chem Rev 86:781

    Article  CAS  Google Scholar 

  19. Tietze LF (1984) In: Bartmann W, Trost BM (eds) Selectivity — a goal for synthetic efficiency. Verlag Chemie, Weinheim pp 299

    Google Scholar 

  20. Weinreb SM, Staib RR (1982) Tetrahedron 38:3087

    Article  CAS  Google Scholar 

  21. Sauer J, Sustmann R (1980) Angew Chem Int Ed Engl 19:779

    Article  Google Scholar 

  22. Desimoni G, Tacconi G (1975) Chem Rev 75:651

    Article  CAS  Google Scholar 

  23. Danishefsky SJ (1996) Angew Chem 108:1483; Angew Chem Int Ed Engl 35:1380

    Article  Google Scholar 

  24. Laschat S (1996) Angew Chem 108:313; Angew Chem Int Ed Engl 35:289

    Article  Google Scholar 

  25. Pindur U, Schneider GH (1994) Chem Soc Rev 23:409

    Article  CAS  Google Scholar 

  26. Schultz PG, Lerner RA (1995) Science 269:1835

    Article  CAS  Google Scholar 

  27. Oikawa H, Katayama K, Suzuki Y, Ichihara A (1995) J Chem Soc Chem Commun 1321

    Google Scholar 

  28. Carrol WA, Grieco PA (1993) J Am Chem Soc 115:1164

    Article  Google Scholar 

  29. Bornmann WG, Kuehne ME (1992) J Org Chem 57:1752

    Article  CAS  Google Scholar 

  30. Scott AI (1970) Acc Chem Res 3:151

    Article  CAS  Google Scholar 

  31. Wenkert E (1962) J Am Chem Soc 84:98

    Article  CAS  Google Scholar 

  32. Chapman OL, Engel MR, Springer JP, Clardy JC (1971) J Am Chem Soc 93:6696

    Article  CAS  Google Scholar 

  33. Blanche F, Cameron B, Crouzet J, Debussche L, Thibaut D, Vuilhorgne M, Leeper FJ, Battersby AR (1995) Angew Chem 107:421; Angew Chem Int Ed Engl 34:383

    Article  Google Scholar 

  34. Le Y, Alanine AID, Viswakarma RA, Balachandran S, Leeper FJ, Battersby AR (1994) J Chem Soc Chem Commun 2507

    Google Scholar 

  35. Tietze LF, Schulz G (1997) Chem J Eur 3:523

    Article  CAS  Google Scholar 

  36. Boland W, Pohnert G, Maier I (1995) Angew Chem 107:1717; Angew Chem Int Ed Engl 34:1602

    Article  Google Scholar 

  37. Cherkauskas JP, Klos AM, Borzilleri RM, Sisko J, Weinreb SM (1996) Tetrahedron 52:3135

    Article  CAS  Google Scholar 

  38. Tietze LF, Brumby T, Pretor M, Remberg G (1988) J Org Chem 53:810

    Article  CAS  Google Scholar 

  39. Review: Houk KN, Li Y, Evanseck JD (1992) Angew Chem 104: 711; Angew Chem Int Ed Engl 31:682

    Article  CAS  Google Scholar 

  40. Dewar MJS, Olivella S, Stewart JJP (1986) J Am Chem Soc 108:5771

    Article  CAS  Google Scholar 

  41. Tietze LF, Fennen J, Anders E (1989) Angew Chem 101:1420; Angew Chem Int Ed Engl 28:1371

    Article  CAS  Google Scholar 

  42. Tietze LF, Fennen J, Schulz G, Anders E (1997) Liebigs Ann Chem: in press

    Google Scholar 

  43. Tietze LF, Fennen J, Geißler H, Schulz G, Anders E (1995) Liebigs Ann Chem: 1681

    Google Scholar 

  44. Mellor JM, Merriman GD (1995) Tetrahedron 51:6115

    Article  CAS  Google Scholar 

  45. Gregoire PJ, Mellor JM, Merriman GD (1995) Tetrahedron 51:6133

    Article  CAS  Google Scholar 

  46. McCarrick MA, Wu YD, Houk KN (1992) J Am Chem Soc 114:1499

    Article  CAS  Google Scholar 

  47. McCarrick MA, Wu YD, Houk KN (1993) J Org Chem 58:3330

    Article  CAS  Google Scholar 

  48. Jursic BS, Zdravkovski Z (1994) J Phys Org Chem 7:641

    Article  CAS  Google Scholar 

  49. Jursic BS (1996) J Comp Chem 17:835

    Article  CAS  Google Scholar 

  50. Jursic BS, Zdravkovski Z (1995) J Org Chem 60:3163

    Article  CAS  Google Scholar 

  51. Suárez D, González J, Sordo TL, Sordo JA (1994) J Org Chem 59:8058

    Article  Google Scholar 

  52. Coxon JM, McDonald DQ (1992) Tetrahedron Lett 33:3673

    Article  CAS  Google Scholar 

  53. Tran Huu Dau ME, Flament JP, Lefour JM, Riche C, Grierson DS (1992) Tetrahedron Lett 33:2343

    Article  Google Scholar 

  54. Tietze LF, Geissler H, Fennen J, Brumby T, Brand S, Schulz G (1994) J Org Chem 59:182

    Article  CAS  Google Scholar 

  55. Tietze LF, Bratz M, Machinek R, v. Kiedrowski G (1987) J Org Chem 52:1638

    Article  CAS  Google Scholar 

  56. Tietze LF, Brumby T, Brand S, Bratz M (1988) Chem Ber 121:499

    Article  CAS  Google Scholar 

  57. Gresham TL, Steadman TR (1949) J Am Chem Soc 71:737

    Article  CAS  Google Scholar 

  58. Dale WJ, Sisti AJ (1954) J Am Chem Soc 76:81

    Article  CAS  Google Scholar 

  59. Bonjouklian R, Ruden RA (1977) J Org Chem 42:4095

    Article  CAS  Google Scholar 

  60. Hosomi A, Sakata Y, Sakurai H (1985) Tetrahedron Lett 26:5175

    Article  CAS  Google Scholar 

  61. Hosomi A, Otaka K, Sakurai H (1986) Tetrahedron Lett 27:2881

    Article  CAS  Google Scholar 

  62. Yablonovskaya SD, Shekhtman NM, Antonova ND, Bogatkov SV, Makin SM, Zefirov NS (1970) Zh Org Khim:6871

    Google Scholar 

  63. Achmatowicz O, Jurczak J, Pyrek JS (1975) Rocz Chem 49:1831

    CAS  Google Scholar 

  64. Daniewski WM, Kubak E, Jurczak J (1985) J Org Chem 50:3963

    Article  CAS  Google Scholar 

  65. Ishihara T, Shinjo H, Inoue Y, Ando T (1983) J Fluorine Chem 22:1

    Article  CAS  Google Scholar 

  66. Kirby AJ, Ryder H, Matassa V (1990) J Chem Soc Perkin Trans 1:617.

    Article  Google Scholar 

  67. Danishefsky SJ, Larson ER, Askin D (1982) J Am Chem Soc 104:6457

    Article  CAS  Google Scholar 

  68. Bednarski M, Danishefsky SJ (1983) J Am Chem Soc 105:3716

    Article  CAS  Google Scholar 

  69. Danishefsky SJ, Pearson WP, Harvey DF, Maring CJ, Springer JP (1985) J Am Chem Soc 107:1256

    Article  CAS  Google Scholar 

  70. Bednarski M, Danishefsky SJ (1986) J Am Chem Soc 108:7060

    Article  CAS  Google Scholar 

  71. Danishefsky SJ, Uang BJ, Quallich G (1985) J Am Chem Soc 107:1285

    Article  CAS  Google Scholar 

  72. Mujica MT, Afonso MM, Galindo A, Palenzuela JA (1996) Tetrahedron 52:2167; see also Gould SJ, Eisenberg RL, Hillis LR (1991) Tetrahedron 47:7209

    Article  CAS  Google Scholar 

  73. Corey EJ, Cywin CL, Roper TD (1992) Tetrahedron Lett 33:6907

    Article  CAS  Google Scholar 

  74. Mikami K, Matsukawa S (1994) J Am Chem Soc 116:4077

    Article  CAS  Google Scholar 

  75. Reetz MT, Raguse B, Marth CF, Hügel HM, Bach T, Fox DNA (1992) Tetrahedron 48:5731

    CAS  Google Scholar 

  76. Lattmann E, Coombs J, Hoffmann HMR (1996) Synthesis 171

    Google Scholar 

  77. Page PCB, Williams PH, Collington EW, Finch H (1987) J Chem Soc Chem Commun 756

    Google Scholar 

  78. Maruoka K, Saito S, Yamamoto H (1994) Synlett 439

    Google Scholar 

  79. Van de Weghe P, Collin J (1994) Tetrahedron Lett 35:2545

    Article  Google Scholar 

  80. Forman MA, Dailey WP (1991) J Am Chem Soc 113:2761

    Article  CAS  Google Scholar 

  81. Reetz MT, Gansäuer A (1993) Tetrahedron 49:6025

    Article  CAS  Google Scholar 

  82. Grieco PA, Moher ED (1993) Tetrahedron Lett. 34:5567

    Article  CAS  Google Scholar 

  83. Tamion R, Mineur C, Ghosez L (1995) Tetrahedron Lett 36:8977

    Article  CAS  Google Scholar 

  84. Handy ST, Grieco PA, Mineur C, Ghosez L (1995) Synlett:565

    Google Scholar 

  85. Clive DLJ, Bergstra RJ (1990) J Org Chem 55:1786

    Article  CAS  Google Scholar 

  86. Jurczak J, Tkacz M (1979) J Org Chem 44:3347

    Article  CAS  Google Scholar 

  87. Schmidt RR, Abele W (1982) Angew Chem 94:298; Angew Chem Int Ed Engl 21:302

    CAS  Google Scholar 

  88. Bauer T, Chapius C, Kozak J, Jurczak J (1989) Helv Chim Acta 72:482

    Article  CAS  Google Scholar 

  89. Bauer T, Kozak J, Chapius C, Jurczak J (1990) J Chem Soc Chem Commun 1178.

    Google Scholar 

  90. David S, Eustache J (1979) J Chem Soc Perkin Trans 1:2230; 2521

    Article  Google Scholar 

  91. David S, Eustache J, Lubineau A (1974) J Chem Soc Perkin Trans 1:2274

    Article  Google Scholar 

  92. Mulzer J, Meyer F, Buschmann J, Luger P (1995) Tetrahedron Lett 36:3503

    Article  CAS  Google Scholar 

  93. Whitesell JK, Lawrence RM, Chen HH (1986) J Org Chem 51:4779

    Article  CAS  Google Scholar 

  94. Lehmler HJ, Nieger M, Breitmaier E (1996) Synthesis 105

    Google Scholar 

  95. Arai Y, Masuda T, Masaki Y, Shiro M (1996) Tetrahedron Asymmetry 7:1199

    Article  CAS  Google Scholar 

  96. Danishefsky SJ, Kobayashi S, Kerwin JF (1982) J Org Chem 47:1981

    Article  CAS  Google Scholar 

  97. Garner P, Ramakanth S (1986) J Org Chem 51:2609

    Article  CAS  Google Scholar 

  98. Midland MM, Afonso MM (1989) J Am Chem Soc 111:4368

    Article  CAS  Google Scholar 

  99. Midland MM, Koops RW (1990) J Org Chem 55:4647; 5058

    Article  CAS  Google Scholar 

  100. Savard J, Brassard P (1979) Tetrahedron Lett 51:4911

    Article  Google Scholar 

  101. Reetz MT, Drewes MW, Schmitz A (1987) Angew Chem 99:1186; Angew Chem Int Ed Engl 26:1141

    Article  CAS  Google Scholar 

  102. Lubineau A, Acrostanzo H, Queneau (1995) J Carb Chem 14:1307

    Article  CAS  Google Scholar 

  103. Lowe RF, Stoodley RJ (1994) Tetrahedron Lett 35:6351

    Article  CAS  Google Scholar 

  104. Faller JW, Smart CJ (1989) Tetrahedron Lett 30:1189

    Article  CAS  Google Scholar 

  105. Maruoka K, Yamamoto H (1989) J Am Chem Soc 111:789

    Article  CAS  Google Scholar 

  106. Maruoka K, Itoh T, Shirasaka T, Yamamoto H (1988) J Am Chem Soc 110:310

    Article  CAS  Google Scholar 

  107. Gao Q, Maruyama T, Mouri M, Yamamoto H (1992) J Org Chem 57:1951

    Article  CAS  Google Scholar 

  108. Mikami K, Motoyama Y, Terada M (1994) J Am Chem Soc 116:2812

    Article  CAS  Google Scholar 

  109. Motoyama Y, Terada M, Mikami K (1995) Synlett 967

    Google Scholar 

  110. Gao Q, Ishihara K, Maruyama T, Mouri M, Yamamoto H (1994) Tetrahedron 50:979

    Article  CAS  Google Scholar 

  111. Keck GE, Li YL, Krishnamurthy D (1995) J Org Chem 60:5998

    Article  CAS  Google Scholar 

  112. Togni A (1990) Organometallics 9:3106

    Article  CAS  Google Scholar 

  113. Johannsen M, Jørgensen KA (1995) J Org Chem 60:5757

    Article  CAS  Google Scholar 

  114. Johannsen M, Jørgensen KA (1996) Tetrahedron 52:7321

    Article  CAS  Google Scholar 

  115. Corey EJ, Cywin CL, Roper TD (1992) Tetrahedron Lett 33:6907

    Article  CAS  Google Scholar 

  116. Salem L (1968) J Am Chem Soc 90:543, 553

    Article  CAS  Google Scholar 

  117. Klopman G (1968) J Am Chem Soc 90:223

    Article  CAS  Google Scholar 

  118. Sauer J, Sustmann R (1980) Angew Chem 92:773; Angew Chem Int Ed Engl 19:779

    Article  CAS  Google Scholar 

  119. Coda AC, Desimoni G, Righetti PP, Tacconi G, Butlafava A, Martinotti-Fancitano F (1983) Tetrahedron 39:331

    Article  Google Scholar 

  120. Snowden RL, Sonnay P, Ohloff G (1981) Helv Chim Acta 64:1247; Woods GF, Sanders H (1946) J Am Chem Soc 68:2483

    Article  Google Scholar 

  121. Tietze LF (1974) Chem Ber 107:2491

    Article  CAS  Google Scholar 

  122. Tietze LF, Glüsenkamp KH, Harms K, Remberg G, Sheldrick GM (1982) Tetrahedron Lett 23:1147

    Article  CAS  Google Scholar 

  123. Tietze LF, Glüsenkamp KH, Holla W (1982) Angew Chem 94:793; Angew Chem Int Ed Engl 21:787

    CAS  Google Scholar 

  124. Tietze LF, Glüsenkamp KH (1983) Angew Chem 95:901; Angew Chem Int Ed Engl 22:887

    CAS  Google Scholar 

  125. Tietze LF, Stegelmeier H, Harms K, Brumby T (1982) Angew Chem 94:868; Angew Chem Int Ed Engl 21:863

    CAS  Google Scholar 

  126. Tietze LF, von Kiedrowski G, Harms K, Clegg W, Sheldrick GM (1980) Angew Chem 92:130; Angew Chem Int Ed Engl 19:134

    Article  CAS  Google Scholar 

  127. Tietze LF, Brumby T, Pfeiffer T (1988) Liebigs Ann Chem 9

    Google Scholar 

  128. Tietze LF, Ott C, Gerke K, Buback M (1993) Angew Chem 105:1536; Angew Chem Int Ed Engl 32, 1485

    Article  CAS  Google Scholar 

  129. Tietze LF, Schäfer P, unpublished results

    Google Scholar 

  130. Tietze LF, Meier H, Nutt H (1989) Chem. Ber. 122:643

    Article  CAS  Google Scholar 

  131. Tietze LF, Meier H, Nutt H (1990) Liebigs Ann Chem 253

    Google Scholar 

  132. Mizukami S, Kihara N, Endo T (1993) Tetrahedron Lett 34:7437

    Article  CAS  Google Scholar 

  133. Koser S, Hoffmann HMR (1994) Heterocycles 37:661

    CAS  Google Scholar 

  134. Weichert A, Hoffmann HMR (1991) J Org Chem 56:4098

    Article  CAS  Google Scholar 

  135. Hoffmann HMR, Gassner A, Eggert U (1991) Chem Ber 124:2475

    Article  CAS  Google Scholar 

  136. De Keyser JL, De Cock CJC, Poupaert JH, Dumont P (1988) J Org Chem 53:4859

    Article  Google Scholar 

  137. Zia-Ebrahimi M, Huffmann GW (1996) Synthesis 215

    Google Scholar 

  138. Bogdanowicz-Szwed K, Palasz A (1995) Monatshefte Chem 126:1341

    CAS  Google Scholar 

  139. Tietze LF, Voß E, Harms K, Sheldrick GM (1985) Tetrahedron Lett 26:5273

    Article  CAS  Google Scholar 

  140. Hojo M, Masuda R, Okada E (1990) Synthesis 347

    Google Scholar 

  141. Hojo M, Masuda R, Okada E (1989) Synthesis 215

    Google Scholar 

  142. Yamauchi M, Katayama S, Baba O, Watanabe T (1990) J Chem Soc Perkin Trans 1:3041

    Article  Google Scholar 

  143. Bloxhan J, Dell CP (1993) J Chem Soc Perkin Trans 1:3055

    Article  Google Scholar 

  144. Dell CP (1992) Tetrahedron Lett 33:699

    Article  CAS  Google Scholar 

  145. Takaki K, Yamada M, Negoro K (1982) J Org Chem 47:5246

    Article  CAS  Google Scholar 

  146. Apparao S, Maier ME, Schmidt RR (1987) Synthesis 896; 900

    Article  Google Scholar 

  147. Tietze LF, Hartfiel U, Hübsch T, Voß E, Bogdanowicz-Szwed K, Wichmann J (1991) Liebigs Ann Chem 275

    Google Scholar 

  148. Tietze LF, Fennen J, Wichmann J (1992) Chem Ber 125:1507

    Article  CAS  Google Scholar 

  149. Tietze LF, Hartfiel U, Hübsch T, Voß E, Wichmann J (1991) Chem. Ber 124:881

    Article  CAS  Google Scholar 

  150. Boger DL, Robarge KD (1988) J Org Chem 53:3373

    Article  CAS  Google Scholar 

  151. Sera A, Ohara M, Yamada H, Egashira E, Ueda N, Setsune J (1994) Bull Chem Soc Jpn 67:1912

    Article  CAS  Google Scholar 

  152. Sera A, Ohara M, Yamada H, Egashira E, Ueda N, Setsune J (1990) Chem Lett 2043

    Google Scholar 

  153. John RA, Schmid V, Wyler H (1987) Helv Chim Acta 70:600

    Article  CAS  Google Scholar 

  154. Zhuo JC, Wyler W (1993) Helv Chim Acta 76:1916

    Article  CAS  Google Scholar 

  155. Zhuo JC, Wyler W, Schenk K (1995) Helv Chim Acta 78: 151

    Article  CAS  Google Scholar 

  156. Hashem MA, Hossain T (1995) Ind J Chem 34B:768

    CAS  Google Scholar 

  157. Coleman RS, Grant EB (1990) Tetrahedron Lett 31:3677

    Article  CAS  Google Scholar 

  158. Pale P, Bouquant J, Chuche J, Carrupt PA, Vogel P (1994) Tetrahedron 50:8035

    Article  CAS  Google Scholar 

  159. Croce PD, Ferraccioli R, La Rosa C (1993) Gass Chim Ital 123:35

    Google Scholar 

  160. Yamamoto Y, Suzuki H, Moro-Oka Y (1986) Chem Lett 73

    Google Scholar 

  161. Wada E, Yasuoka H, Kanemasa S (1994) Chem Lett 145

    Google Scholar 

  162. Wada E, Pei W, Yasuoka H, Chin U, Kanemasa S (1996) Tetrahedron 52:1205

    Article  CAS  Google Scholar 

  163. Mérour J-Y, Chichereau L, Desarbre E, Gadonneix P (1996) Synthesis 519

    Google Scholar 

  164. Conrads M, Mattay J, Runsink J (1989) Chem Ber 122:2207

    Article  CAS  Google Scholar 

  165. Desimoni G, Faita G, Righetti PP, Tacconi G (1991) Tetrahedron 47:8399

    Article  CAS  Google Scholar 

  166. Desimoni G, Faita G, Righetti PP, Toma L (1990) Tetrahedron 46:7951

    Article  CAS  Google Scholar 

  167. Corsico Coda A, Desimoni G, Faita G, Righetti PP, Tacconi G (1989) Tetrahedron 45:775

    Article  Google Scholar 

  168. Grieco PA, Nunes JJ, Gaul MD (1990) J Am Chem Soc 112:4595

    Article  CAS  Google Scholar 

  169. Desimoni G, Faita G, Righetti PP, Vietti F (1995) Heterocycles 40:817

    CAS  Google Scholar 

  170. Desimoni G, Faita G, Righetti PP (1995) Tetrahedron Lett 36:2855

    Article  CAS  Google Scholar 

  171. Desimoni G, Faita G, Righetti PP, Jardone N (1996) personal communication 161.

    Google Scholar 

  172. Tietze LF, Schneider C, Grote A (1996) Chem Eur J 2:139

    Article  CAS  Google Scholar 

  173. Tietze LF, Schneider C, Montenbruck A (1994) Angew Chem 106:1031 Angew Chem Int Ed Engl 33: 980

    Article  CAS  Google Scholar 

  174. Tietze LF, Hartfiel U (1990) unpublished results

    Google Scholar 

  175. Tietze LF, Schulz G (1995) Liebigs Ann Chem 1921

    Google Scholar 

  176. Tietze LF, Schneider C (1992) Synlett 755

    Google Scholar 

  177. Snider BB, Zhang Q (1991) J Org Chem 56:4908

    Article  CAS  Google Scholar 

  178. Evans DA, Chapman KT, Bisaha J (1984) J Am Chem Soc 106:4261 (1989) 110:1238

    Article  CAS  Google Scholar 

  179. Tietze LF, Brand S, Pfeiffer T, Antel J, Harms K, Sheldrick GM (1987) J Am Chem Soc 109:921

    Article  CAS  Google Scholar 

  180. Sakaki J, Sugita Y, Sato M, Kaneko C (1991) Tetrahedron 47:6197

    Article  CAS  Google Scholar 

  181. Sato M, Kano K, Kitazawa N, Hisamichi H, Kaneko C (1990) Heterocycles 31:1229

    CAS  Google Scholar 

  182. Sato M, Kitazawa N, Nagashima S, Kaneko C, Inoue N, Furuya (1991) Tetrahedron 47:7271

    Article  CAS  Google Scholar 

  183. Sato M, Sunami S, Kaneko C, Satoh S, Furuya T (1994) Tetrahedron: Asymmetry 5:1665

    Article  CAS  Google Scholar 

  184. Tietze LF, Beifuss U, Ruther M, Rühlmann A, Antel J, Sheldrick GM (1988) Angew Chem 100:1200; Angew Chem Int Ed Engl 27:1186

    Article  CAS  Google Scholar 

  185. Tietze LF, Schulz G. (1996) Liebigs Ann 1575

    Google Scholar 

  186. Hiroi K, Umemura M, Tomikawa Y (1993) Heterocycles 35:73

    Article  CAS  Google Scholar 

  187. Hiroi K, Umemura M, Fujisawa A (1992) Tetrahedron Lett 33:7161

    Article  CAS  Google Scholar 

  188. Dondoni A, Kniezo L, Martinkova M (1994) J Chem Soc Chem Commun 963

    Google Scholar 

  189. Dondoni A, Kniezo L, Martinkova M, Imrich J (1997) Chem J Eur 3:424

    CAS  Google Scholar 

  190. Lopez JC, Lameignere E, Lukacs G (1988) J Chem Soc Chem Commun 514

    Google Scholar 

  191. Tietze LF, Saling P (1992) Synlett 281

    Google Scholar 

  192. Tietze LF, Saling P (1993) Chirality 5:329

    Article  CAS  Google Scholar 

  193. Wada E, Yasuoka H, Kanemasa S (1994) Chem Lett 1637

    Google Scholar 

  194. Wada E, Pei W, Yasuoka H, Chin U, Kanemasa S (1996) Tetrahedron 52:1205

    Article  CAS  Google Scholar 

  195. Alder K (1943) Neuere Methoden der präparativen organischen Chemie, Verlag Chemie, Weinheim/Germany

    Google Scholar 

  196. Padwa A, Gareau Y, Harrison B, Norman BH (1991) J Org Chem 56:2713

    Article  CAS  Google Scholar 

  197. Le Coz L, Veyrat-Martin C, Wartski L, Seyden-Penne J, Bois C, Philoche-Levisalles M (1990) J Org Chem 55:4870

    Article  Google Scholar 

  198. The use of lanthanide triflates as catalysts for imino-Diels-Alder reactions has been described very recently in a feature article: Kobayashi S, Ishitani H, Nagayama S (1995) Synthesis 1195

    Google Scholar 

  199. Waldmann H, Braun M, Dräger H (1991) Tetrahedron: Asymmetry 2:1231; for a review see: Waldmann H (1995) Synlett 133

    Article  CAS  Google Scholar 

  200. Lock R, Waldmann H (1994) Liebigs Ann Chem 511

    Google Scholar 

  201. Waldmann H, Braun M (1991) Liebigs Ann Chem 1045

    Google Scholar 

  202. Waldmann H (1989) Liebigs Ann Chem 231

    Google Scholar 

  203. Lock R, Waldmann H (1996) Tetrahedron Lett 37:2753

    Article  CAS  Google Scholar 

  204. Waldmann H, Braun M (1992) J Org Chem 57:4444

    Article  CAS  Google Scholar 

  205. Waldmann H, Braun M, Weymann M, Gewehr M (1991) Synlett 881

    Google Scholar 

  206. Kunz H, Pfrengle W (1989) Angew. Chem 101: 1041; Angew Chem Int Ed Engl 28:1067

    CAS  Google Scholar 

  207. Herczegh P, Kovács I, Szilágyi L, Sztaricskai F, Berecibar A, Riche C, Chiaroni A, Olesker A, Lukacs G (1995) Tetrahedron 51:2969

    Article  CAS  Google Scholar 

  208. Herczegh P, Kovács I, Szilágyi L, Sztaricskai F (1994) Tetrahedron 50:13671

    Article  CAS  Google Scholar 

  209. Herczegh P, Kovács I, Szilágyi L, Zsély M, Sztaricskai F (1992) Tetrahedron Lett 33:3133

    Article  CAS  Google Scholar 

  210. Kündig EP, Xu LH, Romanens P, Bernardinelli G (1996) Synlett 270

    Google Scholar 

  211. Baldoli C, Del Buttero P, Di Ciolo M, Maiorana S, Papagni A (1996) Synlett 258

    Google Scholar 

  212. Bailey PD, Londesbrough DJ, Hancox TC, Heffernan JD, Holmes AB (1994) J Chem Soc Chem Comm 2543

    Google Scholar 

  213. Bailey PD, Brown GR, Korber F, Reed A, Wilson RD (1991) Tetrahedron Asymmetry 2:1263

    Article  CAS  Google Scholar 

  214. Bailey PD, Wilson RD, Brown GR (1991) J Chem Soc Perkin Trans 1:1337

    Article  Google Scholar 

  215. Ishihara K, Miyata M, Hattori K, Tada T, Yamamoto H (1994) J Am Chem Soc 116:10520

    Article  CAS  Google Scholar 

  216. Hattori K, Yamamoto H (1993) Tetrahedron 49:1749

    Article  CAS  Google Scholar 

  217. Hattori K, Yamamoto H (1993) Synlett 129

    Google Scholar 

  218. Hamley P, Helmchen G, Holmes AB, Marshall DR, MacKinnon JWM, Smith DF, Ziller JW (1992) J Chem Soc Chem Comm 786

    Google Scholar 

  219. McFarlane AK, Thomas G, Whiting A (1995) J Chem Soc Perkin Trans 1:2803

    Article  Google Scholar 

  220. McFarlane AK, Thomas G, Whiting A (1993) Tetrahedron Lett 43:2379

    Article  Google Scholar 

  221. Abraham H, Théus E, Stella L (1994) Bull Soc Chim Belg 103:361

    CAS  Google Scholar 

  222. Abraham H, Stella L (1992) Tetrahedron 48:9707

    Article  CAS  Google Scholar 

  223. Lease TG, Shea KJ (1993) J Am Chem Soc 115:2248

    Article  CAS  Google Scholar 

  224. Midland MM, Koops RW (1992) J Org Chem 57:1158

    Article  CAS  Google Scholar 

  225. Barluenga J, Aznar F, Valdés C, Martín A, García-Granda S, Martín E (1993) J Am Chem Soc 115:4403; for diastereoselective aza-Diels-Alder reactions of achiral 2-amino-1,3-butadienes see:Barluenga J, Aznar F, Valdés C, Cabal M-P (1993) J Org Chem 58:3391

    Article  CAS  Google Scholar 

  226. For further applications of chiral 2-amino-1,3-butadienes see: Krohn K (1993) Angew Chem 105:1651; Angew Chem Int Ed Engl 32:1582; Enders D, Meyer O (1996) Liebigs Ann 1023

    Article  CAS  Google Scholar 

  227. Katagiri N, Kurimoto A, Kitano K, Nochi H, Sato H, Kaneko C (1992) Nucleic Acids Symp Ser 27:83

    CAS  Google Scholar 

  228. Kappe CO, Wentrup C, Kollenz G (1993) Monatsh Chem 124:1133

    CAS  Google Scholar 

  229. Grieco PA, Clark JD (1990) J Org Chem 55:2271

    Article  CAS  Google Scholar 

  230. Grieco PA, Parker DT, Fobare WF, Ruckle R (1987) J Am Chem Soc 109:5859

    Article  CAS  Google Scholar 

  231. Grieco PA, Bahsas A (1987) J Org Chem 52:5746

    Article  CAS  Google Scholar 

  232. Katritzky AR, Gordeev MF (1993) J Org Chem 58:4049

    Article  CAS  Google Scholar 

  233. Tietze LF, Fennen J, Geissler H, Schulz G, Anders E (1995) Liebigs Ann 1681. For further theoretical analysis of aza-Diels-Alder reactions see:Tran Huu Dau ME, Flament JP, Lefour L-M, Riche C, Grierson DS (1992) Tetrahedron Lett 33:2343; Bachrach SM, Liu M (1992) J Org Chem 57:6736

    Google Scholar 

  234. For an examplary transformation see: Vijn RJ, Arts HJ, Green R, Castelijns AM (1994) Synthesis 573

    Google Scholar 

  235. For a general discussion see ref. 14

    Google Scholar 

  236. Ghosez L, Serckx-Poncin B, Rivera M, Bayard P, Sainte F, Demoulin A, Hesbain-Frisque A-M, Mockel A, Munoz L, Bernard-Henriet C (1985) Lect Heterocycl Chem 8:69

    CAS  Google Scholar 

  237. Serckx-Poncin B, Hesbain-Frisque A-M, Ghosez L (1982) Tetrahedron Lett 23:3261

    Article  CAS  Google Scholar 

  238. Del Mar Blanco M, Alonso MA, Avendano C, Menéndez JC (1996) Tetrahedron 52:5933

    Article  Google Scholar 

  239. Tapia RA, Quintanar C, Valderrama JA (1996) Heterocycles 43:447

    CAS  Google Scholar 

  240. Chaker L, Pautet F, Fillion H (1995) Heterocycles 41:1169

    CAS  Google Scholar 

  241. Brassard P, Lévesque S, (1994) Heterocycles 38:2205

    Google Scholar 

  242. Gómez-Bengoa E, Echavarren AM (1991) J Org Chem 56:3497

    Article  Google Scholar 

  243. Kitahara Y, Kubo A (1992) Heterocycles 34:1089

    CAS  Google Scholar 

  244. Beaudegnies R, Ghosez L (1994) Tetrahedron Asymmetry 5:557

    Article  CAS  Google Scholar 

  245. Waldner A (1989) Tetrahedron Lett 30:3061

    Article  CAS  Google Scholar 

  246. Boger DL, Zhu Y (1991) Tetrahedron Lett 32:7643

    Article  CAS  Google Scholar 

  247. Behforouz M, Gu Z, Cai W, Horn MA, Ahmadian M (1993) J Org Chem 58:7089

    Article  CAS  Google Scholar 

  248. Pérez JM, Avendano C, Menéndez JC (1995) Tetrahedron 51:6573

    Article  Google Scholar 

  249. Boger DL, Corbett WL, Curran TT, Kasper AM (1991) J Am Chem Soc 113:1713

    Article  CAS  Google Scholar 

  250. Boger DL, Nakahara S (1991) J Org Chem 56:880

    Article  CAS  Google Scholar 

  251. Boger DL, Corbett WL, Wiggins JM (1990) J Org Chem 55:2999

    Article  CAS  Google Scholar 

  252. Boger DL, Kasper AM (1989) J Am Chem Soc 111:1517

    Article  CAS  Google Scholar 

  253. Boger DL, Corbett WL (1993) J Org Chem 58:2068

    Article  CAS  Google Scholar 

  254. Uyehara T, Chiba N, Suzuki I, Yamamoto Y (1991) Tetrahedron Lett 32:4371

    Article  CAS  Google Scholar 

  255. Teng M, Fowler FW (1990) J Org Chem 55:5646

    Article  CAS  Google Scholar 

  256. Uyehara T, Suzuki I, Yamamoto Y (1990) Tetrahedron Lett 31:3753

    Article  CAS  Google Scholar 

  257. Hwang YC, Fowler FW (1985) J Org Chem 50:2719

    Article  CAS  Google Scholar 

  258. Jung ME, Choi YM (1991) J Org Chem 56:6729

    Article  CAS  Google Scholar 

  259. Wojciechowski K (1993) Tetrahedron 49:7277

    Article  CAS  Google Scholar 

  260. Wojciechowski (1991) Synlett 571

    Google Scholar 

  261. Dufour B, Motorina I, Fowler FW, Grierson DS (1994) Heterocycles 37:1455

    CAS  Google Scholar 

  262. Trione C, Toledo LM, Kuduk SD, Fowler FW, Grierson DS (1993) J Org Chem 58: 2075

    Article  CAS  Google Scholar 

  263. Teng M, Fowler FW (1989) Tetrahedron Lett 30:2481; see also ref. 237

    Article  CAS  Google Scholar 

  264. Sisti NJ, Motorina IA, Tran Huu Dau M-E, Riche C, Fowler FW, Grierson DS (1996) J Org Chem 61:3715

    Article  CAS  Google Scholar 

  265. Sisti NJ, Fowler FW, Grierson DS (1991) Synlett 816

    Google Scholar 

  266. Sakamoto M, Nagano M, Suzuki Y, Satoh K, Tamura O (1996) Tetrahedron 52:733

    Article  CAS  Google Scholar 

  267. Echavarren AM (1990) J Org Chem 55:4255; see also Nebois P, Fillion H, Benameur L (1993) Tetrahedron 49:9767

    Article  CAS  Google Scholar 

  268. Gürtler CF, Steckhan E, Blechert S (1996) J Org Chem 61:4136

    Article  Google Scholar 

  269. Gürtler CF, Steckhan E, Blechert S (1995) Angew Chem 107:2025; Angew Chem Int Ed Engl 34:1900

    Article  Google Scholar 

  270. Bouaziz Z, Nebois P, Fillion H (1995) Tetrahedron 51:4057

    Article  CAS  Google Scholar 

  271. Villacampa M, Pérez JM, Avendaño C, Menéndez JC (1994) Tetrahedron 50:10047.

    Article  CAS  Google Scholar 

  272. For a recent study concerning lanthanide triflates in hetero-Diels-Alder reactions of 2-azabutadienes see: Makioka Y, Shindo T, Taniguchi Y, Takaki K, Fujiwara Y (1995) Synthesis 801

    Google Scholar 

  273. Mellor JM, Merriman GD (1995) Tetrahedron 51:6115

    Article  CAS  Google Scholar 

  274. Mellor JM, Merriman GD, Riviere P (1991) Tetrahedron Lett 32:7103

    Article  CAS  Google Scholar 

  275. Linkert F, Laschat S, Kotila S, Fox T (1996) Tetrahedron 52:955

    Article  CAS  Google Scholar 

  276. Mellor JM, Merriman GD (1995) Steroids 60:693

    Article  CAS  Google Scholar 

  277. Gregoire PJ, Mellor JM, Merriman GD (1991) Tetrahedron Lett 32:7099

    Article  CAS  Google Scholar 

  278. Grieco PA, Bahsas A (1988) Tetrahedron Lett 29:5855

    Article  CAS  Google Scholar 

  279. Barluenga J, Joglar J, González FJ, Fustero S (1990) Synlett 129, and references cited therein

    Google Scholar 

  280. Barluenga J, Joglar J, González FJ, Fustero S, Krüger C, Tsay Y-H (1991) Synthesis 387

    Google Scholar 

  281. Barluenga J, Joglar J, González FJ, Fustero S (1989) Tetrahedron Lett 30:2001

    Article  CAS  Google Scholar 

  282. Barluenga J, González FJ, García-Granda S, Pérez-Carreño E (1991) J Org Chem 56:4459

    Article  CAS  Google Scholar 

  283. Barluenga J, González FJ, Fustero S (1990) Tetrahedron Lett 31:397; see also ref. 261

    Article  CAS  Google Scholar 

  284. Barluenga J, Pérez Carlón R, González FJ, Joglar J, López Ortiz F, Fustero S (1992) Bull Soc Chim Fr 129:566

    Google Scholar 

  285. Barluenga J, Pérez Carlón R, González FJ, López Ortiz F, Fustero S (1991) J Chem Soc Chem Comm 1704

    Google Scholar 

  286. Tietze LF, Utecht J (1992) Chem Ber 125:2259

    Article  CAS  Google Scholar 

  287. For a recent study concerning intermolecular aza-Diels-Alder reactions of N-aryl imines see: Narasaka K, Shibata T (1993) Heterocycles 35:1039

    CAS  Google Scholar 

  288. Linkert F, Laschat S, Knickmeier M (1995) Liebigs Ann 985

    Google Scholar 

  289. Temme O, Laschat S (1995) J Chem Soc Perkin Trans 1:125

    Article  Google Scholar 

  290. Linkert F, Laschat S (1994) Synlett 125

    Google Scholar 

  291. Laschat S, Lauterwein J (1993) J Org Chem 58:2856

    Article  CAS  Google Scholar 

  292. Laschat S, Noe R, Riedel M, Krüger C (1993) Organometallics 12:3738

    Article  CAS  Google Scholar 

  293. Beifuss U, Herde A, Ledderhose S (1996) J Chem Soc Chem Comm 1213. For mechanistic studies on cycloadditions of isoquinolinium salts see: Gupta RB, Franck RW (1987) J Am Chem Soc 109:5393

    Google Scholar 

  294. Beifuss U, Kunz O, Ledderhose S, Taraschewski M, Tonko C (1996) Synlett 34

    Google Scholar 

  295. Beifuss U, Ledderhose S (1995) J Chem Soc Chem Comm 2137

    Google Scholar 

  296. Barluenga J, Tomás M, Ballesteros A, Gotor V (1989) J Chem Soc Chem Comm 267

    Google Scholar 

  297. Bayard P, Ghosez L (1988) Tetrahedron Lett 29:6115

    Article  CAS  Google Scholar 

  298. Bayard P, Sainte F, Beaudegnies R, Ghosez L (1988) Tetrahedron Lett 29:3799

    Article  Google Scholar 

  299. Sainte F, Serckx-Poncin B, Hesbain-Frisque A-M, Ghosez L (1982) J Am Chem Soc 104: 1428

    Article  CAS  Google Scholar 

  300. Gouverneur V, Ghosez L (1991) Tetrahedron Lett 32:5349, for a study on analogous reactions involving achiral nitroso dienophiles see: Gouverneur V, Ghosez L (1996) Tetrahedron 52:7585

    Article  CAS  Google Scholar 

  301. Pouilhès A, Langlois Y, Nshimyumukiza P, Mbiya K, Ghosez L (1993) Bull Soc Chim Fr 130:304

    Google Scholar 

  302. Nakahara S, Numata R, Tanaka Y, Kubo A (1995) Heterocycles 41:651

    Article  CAS  Google Scholar 

  303. Bouammali B, Pautet F, Fillion H (1993) Tetrahedron 49:3125

    Article  CAS  Google Scholar 

  304. Saito T, Ohkubo T, Maruyama K, Kuboki H, Motoki S (1993) Chem Lett 1127

    Google Scholar 

  305. Molina P, Alajarín M, Vidal A, Sánchez-Andrada P (1992) J Org Chem 57:929

    Article  CAS  Google Scholar 

  306. Molina P, Arques A, Molina A (1991) Synthesis 21

    Google Scholar 

  307. Paquette LA, Branan BM, Rogers RD (1995) J Org Chem 60:1852

    Article  CAS  Google Scholar 

  308. Barluenga J, Tomás M, Suárez-Sobrino A, López LA (1995) J Chem Soc Chem Comm 1785; for an analogous transformation with an achiral aminodiene see: Barluenga J, Aznar F, Fernández M (1995) Tetrahedron Lett 36:6551

    Google Scholar 

  309. Enders D, Meyer O, Raabe G, Runsink J (1994) Synthesis 66

    Google Scholar 

  310. Tripathy R, Franck RW, Onan KD (1988) J Am Chem Soc 110:3257

    Article  CAS  Google Scholar 

  311. Thiem R, Rotscheidt K, Breitmeier E (1989) Synthesis 836

    Google Scholar 

  312. Kerrigan JE, McDougal PG, VanDerveer D (1993) Tetrahedron Lett 34:8055

    Article  CAS  Google Scholar 

  313. Sapinall IH, Cowley PM, Stoodley RJ (1994) Tetrahedron Lett 35:3397

    Article  Google Scholar 

  314. Aspinall IH, Cowley PM, Mitchell G, Stoodley RJ (1993) J Chem Soc Chem Comm 1179

    Google Scholar 

  315. Tsuge O, Hatta T, Yakata K, Maeda H (1994) Chem Lett 1833

    Google Scholar 

  316. Jenner G, Ben Salem R (1990) J Chem Soc Perkin Trans 2 1961

    Google Scholar 

  317. Guzmán A, Romero M, Talamás FX, Villena R, Greenhouse R, Muchowski JM (1996) J Org Chem 61:2470

    Article  Google Scholar 

  318. Mazumdar SN, Mukherjee S, Sharma AK, Sengupta D, Mahajan MP (1994) Tetrahedron 50:7579

    Article  CAS  Google Scholar 

  319. Mazumdar SN, Mahajan MP (1991) Tetrahedron 47:1473

    Article  CAS  Google Scholar 

  320. Luthardt P, Würthwein E-U (1988) Tetrahedron Lett 29:921

    Article  CAS  Google Scholar 

  321. Sain B, Singh SP, Sandhu JS (1992) Tetrahedron 48:4567

    Article  CAS  Google Scholar 

  322. Sain B, Singh SP, Sandhu JS (1991) Tetrahedron Lett 32:5151

    Article  CAS  Google Scholar 

  323. Barluenga J, Tomás M, Ballesteros A, López LA (1994) Heterocycles 37:1109

    Article  CAS  Google Scholar 

  324. Barluenga J, Tomás M, Ballesteros A, López LA (1989) Tetrahedron Lett 30:4573

    Article  CAS  Google Scholar 

  325. Tietze LF, Utecht J, unpublished results

    Google Scholar 

  326. South MS, Jakuboski TL (1995) Tetrahedron Lett 36:5703

    CAS  Google Scholar 

  327. Ferguson G, Lough AJ, Mackay D, Weeratunga G (1991) J Chem Soc Perkin Trans 1:3361

    Article  Google Scholar 

  328. Ganesan A, Heathcock CH (1993) J Org Chem 58:6155

    Article  CAS  Google Scholar 

  329. Stolle WAW, Frissen AE, Marcelis ATM, van der Plas HC (1992) J Org Chem 57:3000

    Article  CAS  Google Scholar 

  330. Stolle WAW, Veurink JM, Marcelis ATM, van der Plas HC (1992) Tetrahedron 48:1643

    Article  CAS  Google Scholar 

  331. Haider N (1992) Tetrahedron 48:7173

    Article  CAS  Google Scholar 

  332. Haider N (1991) Tetrahedron 47:3959

    Article  CAS  Google Scholar 

  333. Nesi R, Giomi D, Turchi S, Falai A (1995) J Chem Soc Chem Comm 2201

    Google Scholar 

  334. Nesi R, Giomi D, Turchi S, Paoli P (1994) Tetrahedron 50:9189

    Article  CAS  Google Scholar 

  335. Boger DL, Kochanny MJ (1994) J Org Chem 59:4950

    Article  CAS  Google Scholar 

  336. Boger DL, Honda T, Menezes RF, Colletti SL, Dang Q, Yang W (1994) J Am Chem Soc 116:82

    Article  CAS  Google Scholar 

  337. Boger DL, Honda T (1994) J Am Chem Soc 116:5647

    Article  CAS  Google Scholar 

  338. Boger DL, Honda T, Menezes RF, Colletti SL (1994) J Am Chem Soc 116:5631

    Article  CAS  Google Scholar 

  339. Boger DL, Honda T, Dang Q (1994) J Am Chem Soc 116:5619

    Article  CAS  Google Scholar 

  340. Boger DL, Menezes RF, Dang Q (1992) J Org Chem 57:4333

    Article  CAS  Google Scholar 

  341. Boger DL, Menezes RF, Honda T (1993) Angew Chem 105:310; Angew Chem Int Ed Engl 32:273

    Article  CAS  Google Scholar 

  342. Boger DL, Dang Q (1992) J Org Chem 57:1630

    Google Scholar 

  343. Li J-H, Snyder JK (1994) Tetrahedron Lett 35: 1485

    Article  CAS  Google Scholar 

  344. Benson SC, Li J-H, Snyder JK (1992) J Org Chem 57: 5285

    Article  CAS  Google Scholar 

  345. Taylor EC, Macor JE, French LG (1991) J Org Chem 56: 1807

    Article  CAS  Google Scholar 

  346. Barlow MG, Sibous L, Suliman NNE, Tipping AE (1996) J Chem Soc Perkin Trans 1:519

    Article  Google Scholar 

  347. Taylor EC, French LG (1989) J Org Chem 54:1245

    Article  CAS  Google Scholar 

  348. Boger DL, Zhang M (1991) J Am Chem Soc 113:4230

    Article  CAS  Google Scholar 

  349. Boger DL, Baldino CM (1993) J Am Chem Soc 115:11418

    Article  CAS  Google Scholar 

  350. Streith J, Defoin A (1996) Synlett 189

    Google Scholar 

  351. Gouverneur V, Ghosez L (1990) Tetrahedron Asymmetry 1:363, see also ref. 282

    Article  CAS  Google Scholar 

  352. Defoin A, Brouillard-Poichet A, Streith J (1992) HelvChimActa 75:109

    CAS  Google Scholar 

  353. Defoin A, Brouillard-Poichet A, Streith J (1991) Helv Chim Acta 74:103

    Article  CAS  Google Scholar 

  354. Braun H, Felber H, Kresze G, Schmidtchen FP, Prewo R, Vasella A (1993) Liebigs Ann Chem 261

    Google Scholar 

  355. Felber H, Kresze G, Prewo R, Vasella A (1986) Helv Chim Acta 69:1137

    Article  CAS  Google Scholar 

  356. Werbitzky O, Klier K, Felber H (1990) Liebigs Ann Chem 267

    Google Scholar 

  357. Braun H, Burger W, Kresze G, Schmidtchen FP (1990) Tetrahedron Asymmetry 1:403

    Article  CAS  Google Scholar 

  358. Schürrle K, Beier B, Piepersberg W (1991) J Chem Soc Perkin Trans 1:2407

    Article  Google Scholar 

  359. Defoin A, Sarazin H, Strehler C, Streith J (1994) Tetrahedron Lett 35:5653

    Article  CAS  Google Scholar 

  360. Kirby GW, Nazeer M (1993) J Chem Soc Perkin Trans 1:1397

    Article  Google Scholar 

  361. Miller A, Procter G (1990) Tetrahedron Lett 31:1043; Miller A, Procter G (1990) Tetrahedron Lett 31:1041

    Article  CAS  Google Scholar 

  362. Shustov GV, Rauk A (1995) Tetrahedron Lett 36:5449

    CAS  Google Scholar 

  363. Defoin A, Pires J, Tissot I, Tschamber T, Bur D, Zehnder M, Streith J (1991) Tetrahedron Asymmetry 2:1209

    Article  CAS  Google Scholar 

  364. Behr J-B, Defoin A, Pires J, Streith J, Macko L, Zehder M (1996) Tetrahedron 52:3283

    Article  CAS  Google Scholar 

  365. Defoin A, Pires J, Streith J (1991) Synlett 417

    Google Scholar 

  366. Hussain A, Wyatt PB (1993) Tetrahedron 49:2123

    Article  CAS  Google Scholar 

  367. Fritz H, Henlin JM, Riesen A, Tschamber T, Zehnder M, Streith J (1988) Helv Chim Acta 71:822

    Article  CAS  Google Scholar 

  368. Tschamber T, Craig CJ, Muller M, Streith J (1996) Tetrahedron 52:6201

    Article  CAS  Google Scholar 

  369. Behr J-B, Defoin A, Mahmood N, Streith J (1995) Helv Chim Acta 78:1166

    Article  CAS  Google Scholar 

  370. Behr J-B, Defoin A, Streith J (1994) Heterocycles 37:747

    CAS  Google Scholar 

  371. Ghosh A, Miller MJ (1995) Tetrahedron Lett 36:6399

    Article  CAS  Google Scholar 

  372. Ghosh A, Ritter AR, Miller MJ (1995) J Org Chem 60:5808

    Article  CAS  Google Scholar 

  373. Ritter AR, Miller MJ (1994) J Org Chem 59:4602

    Article  CAS  Google Scholar 

  374. Naruse M, Aoyagi S, Kibayashi C (1996) J Chem Soc Perkin Trans 1:1113

    Article  Google Scholar 

  375. Naruse M, Aoyagi S, Kibayashi C (1994) Tetrahedron Lett 35:9213

    Article  CAS  Google Scholar 

  376. Quadrelli P, Gamba Invernizzi A, Caramella P (1996) Tetrahedron Lett 37:1909

    Article  CAS  Google Scholar 

  377. Soulié J, Betzer J-F, Muller B, Lallemand J-Y (1995) Tetrahedron Lett 36:9485

    Article  Google Scholar 

  378. Naylor (née Bathgate) A, Howarth N, Malpass JR (1993) Tetrahedron 49:451

    Article  Google Scholar 

  379. Kefalas P, Grierson DS (1993) Tetrahedron Lett 34:3555

    Article  CAS  Google Scholar 

  380. Pindur U, Kim M-H (1989) Tetrahedron 45:6427

    Article  CAS  Google Scholar 

  381. Gilchrist TL (1983) Chem Soc Rev 12:53

    Article  CAS  Google Scholar 

  382. Reissig H-U, Hippeli C, Arnold T (1990) Chem Ber 123:2403

    Article  CAS  Google Scholar 

  383. Jursic BS, Zdravkovski Z (1995) J Org Chem 60:3163

    Article  CAS  Google Scholar 

  384. Hippeli C, Reissig H-U (1987) Synthesis 77

    Google Scholar 

  385. Hippeli C, Basso N, Dammast F, Reissig H-U (1990) Synthesis 26

    Google Scholar 

  386. Zimmer R, Reissig H-U (1992) J Org Chem 57:339

    Article  CAS  Google Scholar 

  387. Henning R, Lerch U, Urbach H (1989) Synthesis 265

    Google Scholar 

  388. Nakanishi S, Higuchi M, Flood T (1986) J Chem Soc Chem Comm 30

    Google Scholar 

  389. Hippeli C, Reissig H-U (1990) Liebigs Ann Chem 217

    Google Scholar 

  390. Zimmer R, Reissig H-U (1991) Liebigs Ann Chem 553

    Google Scholar 

  391. Zimmer R, Reissig H-U (1988) Angew Chem 100:1576; Angew Chem Int Ed Engl 27:1518

    Article  CAS  Google Scholar 

  392. Zimmer R, Reissig H-U (1989) Synthesis 908

    Google Scholar 

  393. Zimmer R, Reissig H-U, Lindner HJ (1992) Liebigs Ann Chem 621

    Google Scholar 

  394. Li JP, Newlander KA, Yellin TO (1988) Synthesis 73

    Google Scholar 

  395. Plate R, Nivard RJF, Ottenhijm HCJ (1987) J Chem Soc Perkin Trans 1:2473

    Article  Google Scholar 

  396. Arnold T, Reissig H-U (1990) Synlett 514

    Google Scholar 

  397. Arnold T, Orschel B, Reissig H-U (1992) Angew Chem 104:1084; Angew. Chem Int Ed Engl 31:1033

    Article  CAS  Google Scholar 

  398. Paulini K, Reissig H-U, Rademacher P (1995) J Prakt Chem 337:209

    Article  CAS  Google Scholar 

  399. Paulini K, Gerold A, Reissig H-U (1995) Liebigs Ann 667

    Google Scholar 

  400. Hofmann B, Reissig H-U (1994) Chem Ber 127:2337

    Article  CAS  Google Scholar 

  401. Paulini K, Reissig H-U (1994) Chem Ber 127:685

    Article  CAS  Google Scholar 

  402. Angermann J, Homann K, Reissig H-U, Zimmer R (1995) Synlett 1014

    Google Scholar 

  403. Hippeli C, Reissig H-U (1990) Liebigs Ann Chem 475

    Google Scholar 

  404. Hippeli C, Zimmer R, Reissig H-U (1990) Liebigs Ann Chem 469

    Google Scholar 

  405. Chinchilla R, Bäckvall J-E (1992) Tetrahedron Lett 33:5641

    Article  CAS  Google Scholar 

  406. Denmark SE, Kesler BS, Moon Y-C (1992) J Org Chem 57:4912

    Article  CAS  Google Scholar 

  407. Denmark SE, Schnute ME (1994) J Org Chem 59:4576

    Article  CAS  Google Scholar 

  408. Denmark SE, Marcin LR (1993) J Org Chem 58:3857

    Article  CAS  Google Scholar 

  409. Denmark SE, Marcin LR (1995) J Org Chem 60:3221

    Article  CAS  Google Scholar 

  410. Denmark SE, Schnute ME, Senanayake CBW (1993) J Org Chem 58:1859

    Article  CAS  Google Scholar 

  411. Denmark SE, Stolle A, Dixon JA, Guagnano V (1995) J Am Chem Soc 117:2100

    Article  CAS  Google Scholar 

  412. Denmark SE, Schnute ME, Marcin LR, Thorarensen A (1995) J Org Chem 60:3205

    Article  CAS  Google Scholar 

  413. Papchikhin A, Agback P, Plavec J, Chattopadhyaya J (1993) J Org Chem 58:2874

    Article  CAS  Google Scholar 

  414. Avalos M, Babiano R, Cintas P, Higes FJ, Jimenez JL, Palacios JC, Silva MA (1996) J Org Chem 61:1880

    Article  CAS  Google Scholar 

  415. Kirby GW, Lochead AW, Sheldrake GN (1984) J Chem Soc Chem Comm 922

    Google Scholar 

  416. Baldein JE, Lopez RCG (1983) Tetrahedron 39:1487

    Article  Google Scholar 

  417. Blandon CM, Ferguson IEG, Kirby GW, Lochead AW (1985) J Chem Soc Perkin Trans 1:1541

    Article  Google Scholar 

  418. Hasserodt J, Pritzkow H, Sundermeyer W (1995) Liebigs Ann 95

    Google Scholar 

  419. Choi SS-M, Kirby GW (1991) J Chem Soc Perkin Trans 1:3225

    Article  Google Scholar 

  420. Vedejs E, Eberlein TH, Wilde RG (1988) J Org Chem 53:2220

    Article  CAS  Google Scholar 

  421. Segi M, Takahashi M, Nakajima T, Suga S (1989) Synth Comm 19:2431

    Article  CAS  Google Scholar 

  422. Vedejs E, Stults JS, Wilde RG (1988) J Am Chem Soc 110:5452

    Article  CAS  Google Scholar 

  423. Takahashi T, Kurose N, Koizumi T (1993) Heterocycles 36:1601

    CAS  Google Scholar 

  424. Bonini BF, Mazzanti G, Zani P, Maccagnani G (1988) J Chem Soc Chem Comm 365

    Google Scholar 

  425. Vedejs E, Stults JS (1988) J Org Chem 53:2226

    Article  CAS  Google Scholar 

  426. Revesz L, Siegel RA, Buescher H-H, Marko M, Maurer R, Meigel H (1990) Helv Chim Acta 73:326

    Article  CAS  Google Scholar 

  427. Pinto IL, Buckle DR, Rami HK, Smith DG (1992) Tetrahedron Lett 33:7597

    Article  CAS  Google Scholar 

  428. Adam D, Freer AA, Isaacs NW, Kirby GW, Littlejohn A, Rahman MS (1992) J Chem Soc Perkin Trans 1:1261

    Article  Google Scholar 

  429. Tromm P, Heimgartner H (1988) Helv Chim Acta 71:2071

    Article  CAS  Google Scholar 

  430. Karakasa T, Motoki S (1978) J Org Chem 43:4147, Karakasa T, Motoki S (1979) J Org Chem 44:4151

    Article  CAS  Google Scholar 

  431. Karasaka T, Yamaguchi H, Motoki S (1980) J Org Chem 45:927

    Article  Google Scholar 

  432. Barnish IT, Fishwick CWG, Hill DR (1991) Tetrahedron Lett 32:405

    Article  CAS  Google Scholar 

  433. Gabbutt CD, Hepworth JD, Heron BM (1992) J Chem Soc Perkin Trans 1:2603

    Article  Google Scholar 

  434. Baruah PD, Mukherjee S, Mahajan MP (1990) Tetrahedron 46:1951

    Article  CAS  Google Scholar 

  435. Greif D, Mulst M, Weissenfeis M (1987) Synthesis 456

    Google Scholar 

  436. Blitzke T, Greif D, Kempe R, Pink M, Pulst M, Sicker D, Wilde H (1994) J Prakt Chem 336:163

    Article  CAS  Google Scholar 

  437. Baruah PD, Nongkynrih I, Mahajan MP (1989) Synthesis 631

    Google Scholar 

  438. Murase M, Nishino N, Nara N, Nakanishi Y, Tobinaga S (1994) Heterocycles 37:725

    CAS  Google Scholar 

  439. Barnish IT, Fishwick CWG, Hill DR, Szantay C Jr (1989) Tetrahedron 45:6771

    Article  CAS  Google Scholar 

  440. Barnish IT, Fishwick CWG, Hill DR, Szantay C Jr (1989) Tetrahedron 45:7879

    Article  CAS  Google Scholar 

  441. Barnish IT, Fishwick CWG, Hill DR, Szantay C Jr (1989) Tetrahedron Lett 30:4449

    Article  CAS  Google Scholar 

  442. Saito T, Nagashima M, Karakasa T, Motoki S (1992) J Chem Soc Chem Comm 411

    Google Scholar 

  443. Saito T, Nagashima M, Karasaka T, Motoki S (1990) J Chem Soc Chem Comm 1665

    Google Scholar 

  444. Moriyama S, Karakasa T, Inoue T, Kurashima K, Satsumabayashi S, Saito T (1996) Synlett 72

    Google Scholar 

  445. Saito T, Kimura H, Sakamaki K, Karakasa T, Moriyama S (1996) J Chem Soc Chem Comm 811

    Google Scholar 

  446. Motoki S, Saito T, Karakasa T, Matsushita T, Furono E (1992) J Chem Soc Perkin Trans 1:2943

    Article  Google Scholar 

  447. Motoki S, Saito T, Karakasa T, Kato H, Matsushita T, Hayashibe S (1991) J Chem Soc Perkin Trans 1:2281

    Article  Google Scholar 

  448. Saito T, Karakasa T, Fujii H, Furono E, Suda H, Kobayashi K (1994) J Chem Soc Perkin Trans 1:1359

    Article  Google Scholar 

  449. Bell AS, Fishwick CWG, Reed JE (1996) Tetrahedron Lett 37:123

    Article  CAS  Google Scholar 

  450. Ohno M, Kojima S, Eguchi S (1995) J Chem Soc Chem Comm 565

    Google Scholar 

  451. Ohno M, Kojima S, Shirakawa Y, Eguchi S (1995) Tetrahedron Lett 36:6899; for similar oxa-Diels-Alder reaction leading to pyran-fused fullerenes see: Ohno M, Azuma T, Eguchi S (1993) Chem Lett 1833

    CAS  Google Scholar 

  452. Meier H, Eckes H-L, Niedermann H-P, Kolshorn H (1987) Angew Chem 99:1040; Angew Chem Int Ed Engl 26:1046

    Article  CAS  Google Scholar 

  453. Jacob D, Niedermann H-P, Meier H (1986) Tetrahedron Lett 27:5703

    Article  CAS  Google Scholar 

  454. Saito T, Shizuta T, Kikuchi H, Nakawaga J, Hirotsu K, Ohmura H, Motoki S (1994) Synthesis 727

    Google Scholar 

  455. Moriyama S, Mochizuki T, Ohshima Y, Saito T (1994) Bull Chem Soc Jpn 67:2876

    Article  CAS  Google Scholar 

  456. Beifuss U, Gehm H, Taraschewski M (1996) Synlett 396

    Google Scholar 

  457. Barluenga J, Tomás M, Ballesteros A, López LA (1989) Tetrahedron Lett 30:6923

    Article  CAS  Google Scholar 

  458. Barluenga J, Tomás M, Ballesteros A, López LA (1995) Synthesis 985

    Google Scholar 

  459. Barluenga J, Tomás M, Ballesteros A, López LA (1991) Synlett 93

    Google Scholar 

  460. Barluenga J, Tomás M, Ballesteros A, López LA (1991) J Org Chem 56:5680

    Article  CAS  Google Scholar 

  461. Marchand A, Mauger D, Guingant A, Pradère J-P (1995) Tetrahedron Asymmetry 6:853

    Article  CAS  Google Scholar 

  462. Chehna M, Pradère J-P, Quiniou H, Le Botlan D, Toupet L (1989) Phosphorus, Sulfur, and Silicon 42:15

    Article  CAS  Google Scholar 

  463. Swindell CS, Tao M (1993) J Org Chem 58:5889

    Article  CAS  Google Scholar 

  464. Nair V, Kumar S (1996) J Chem Soc Perkin Trans 1:443

    Article  Google Scholar 

  465. Nair V, Kumar S (1994) J Chem Soc Chem Comm 1341

    Google Scholar 

  466. Dondoni A, Fogagnolo M, Mastellari A, Pedrini P (1986) Tetrahedron Lett 27:3915

    Article  CAS  Google Scholar 

  467. Hartke K, Lindenblatt T (1990) Synthesis 281

    Google Scholar 

  468. Capozzi G, Franck RW, Mattioli M, Menichetti S, Nativi C, Valle G (1995) J Org Chem 60:6416

    Article  CAS  Google Scholar 

  469. Capozzi G, Dios A, Franck RW, Geer A, Marzabadi C, Menichetti S, Nativi C, Tamarez M (1996) Angew Chem 108:805; Angew Chem Int Ed Engl 35:777

    Article  Google Scholar 

  470. Leblanc Y, Fitzsimmons BJ, Springer JP, Rokach J (1989) J Am Chem Soc 111:2995

    Article  CAS  Google Scholar 

  471. Toepfer A, Schmidt RR (1993) Carbohydr Res 247:159

    Article  CAS  Google Scholar 

  472. Weinreb SM (1988) Acc Chem Res 21:313

    Article  CAS  Google Scholar 

  473. Garigipati RS, Cordoba R, Parvez M, Weinreb SM (1986) Tetrahedron 42:2979

    Article  CAS  Google Scholar 

  474. Bell SI, Parvez M, Weinreb SM (1991) J Org Chem 56:373, and literature cited therein

    Article  CAS  Google Scholar 

  475. Turos E, Parvez M, Garigipati RS, Weinreb SM (1988) J Org Chem 53:1116

    Article  CAS  Google Scholar 

  476. Bell SI, Weinreb SM (1988) Tetrahedron Lett 29:4233

    Article  CAS  Google Scholar 

  477. Hamada T, Sato H, Hikota M, Yonemitsu O (1989) Tetrahedron Lett 30:6405

    Article  CAS  Google Scholar 

  478. Tornus I, Schaumann E (1996) Tetrahedron 52:725

    Article  CAS  Google Scholar 

  479. Deguin B, Vogel P (1993) Tetrahedron Lett 34:6269

    Article  CAS  Google Scholar 

  480. Deguin B, Vogel P (1993) Helv Chim Acta 76:2250

    Article  CAS  Google Scholar 

  481. Deguin B, Vogel P (1992) J Am Chem Soc 114:9210

    Article  CAS  Google Scholar 

  482. Suárez D, González J, Sordo TL, Sordo JA (1994) J Org Chem 59:8058

    Article  Google Scholar 

  483. Suárez D, Sordo TL, Sordo JA (1994) J Am Chem Soc 116:763

    Article  Google Scholar 

  484. Suárez D, Assfeld X, González J, Ruiz-López MF, Sordo TL, Sordo JA (1994) J Chem Soc Chem Comm 1683

    Google Scholar 

  485. Gilchrist TL, Wood JE (1992) J Chem Soc Perkin Trans 1:9

    Article  Google Scholar 

  486. Steliou K, Gareau Y, Milot G, Salama P (1990) J Am Chem Soc 112:7819

    Article  CAS  Google Scholar 

  487. Regitz M, Binger P (1988) Angew Chem 100:1541; Angew Chem Int Ed Engl 27:1484

    Article  CAS  Google Scholar 

  488. Märkl G, Dorsch S (1995) Tetrahedron Lett 36:3839; b) Märkl G, Dorfmeister G (1987) Tetrahedron Lett 28:1093

    Article  Google Scholar 

  489. Driess M, Pritzkow H, Rell S, Winkler U (1996) Organometallics 15:1845

    Article  CAS  Google Scholar 

  490. Sekiguchi A, Maruki I, Ebata K, Kabuto C, Sakurai H (1991) J Chem Soc Chem Comm 341

    Google Scholar 

  491. Paetzold P, Kiesgen J, Krahé K, Meier H-U, Boese R (1991) Z Naturforschung (B) 46:853

    CAS  Google Scholar 

  492. Segi M, Kato M, Nakajima T (1991) Tetrahedron Lett 7427

    Google Scholar 

  493. Bauer T, Jezewski A, Jurczak J (1996) Tetrahedron Asymmetry 7: 1405

    Article  CAS  Google Scholar 

  494. Golebiowski A, Jacobsson U, Chmielewski M, Jurczak J (1987) Tetrahedron 43:599

    Article  CAS  Google Scholar 

  495. Lubineau A, Queneau Y (1995) J Carbohydr Chem 14:1295

    Article  CAS  Google Scholar 

  496. Tietze LF, Montenbruck A, Schneider C (1994) Synlett 509; see also ref. 161 and 163

    Google Scholar 

  497. De Gaudenzi L, Apparao S, Schmidt RR (1990) Tetrahedron 46:277

    Article  Google Scholar 

  498. Haag-Zeino B, Schmidt RR (1990) Liebigs Ann Chem 1197

    Google Scholar 

  499. Dujardin G, Rossignol S, Brown E (1996) Tetrahedron Lett 37:4007

    Article  CAS  Google Scholar 

  500. Tietze LF, Bachmann J, Wichmann J, Burkhardt O (1994) Synthesis 1185.

    Google Scholar 

  501. Martin SF, Clark CW, Corbett JW (1995) J Org Chem 60:3236

    Article  CAS  Google Scholar 

  502. Martin SF, Benage B, Geraci LS, Hunter JE, Mortimore M (1991) J Am Chem Soc 113:6161

    Article  CAS  Google Scholar 

  503. Martin SF, Benage B, Unter JE (1988) J Am Chem Soc 110:5925

    Article  CAS  Google Scholar 

  504. Takano S, Ohkawa S, Tamori S, Satoh S, Ogasawara K (1988) J Chem Soc Chem Comm: 189

    Google Scholar 

  505. Takano S, Satoh S, Ogasawara K (1988) J Chem Soc Chem Comm 59

    Google Scholar 

  506. Takano S (1987) Pure Appl Chem 59:353

    Article  CAS  Google Scholar 

  507. Tietze LF, Meier H, Nutt H (1990) Liebigs Ann Chem 253

    Google Scholar 

  508. Tietze LF, Bärtels C (1991) Liebigs Ann Chem 155

    Google Scholar 

  509. Tietze LF, Denzer H, Holdgrün X, Neumann M (1987) Angew. Chem 99:1309; Angew Chem Int Ed Engl 26:1295

    Article  CAS  Google Scholar 

  510. Tietze LF, Wölfling J, Schneider G (1991) Chem Ber 124:591

    Article  CAS  Google Scholar 

  511. Tietze LF, Beifuss U, Lökös M, Rischer M, Göhrt A, Sheldrick GM (1990) Angew Chem 102:545; Angew. Chem Int Ed Engl. 29:527

    Article  CAS  Google Scholar 

  512. Tietze LF, Schneider C (1991) J Org Chem 56:2476

    Article  CAS  Google Scholar 

  513. Ireland RE, Armstrong JD, III, Lebreton J, Meissner RS, Rizzacasa MA (1993) J Am Chem Soc 115:7152

    Article  CAS  Google Scholar 

  514. Snider BB, Lu Q (1996) J Org Chem 61:2839

    Article  CAS  Google Scholar 

  515. Snider BB, Lu Q (1994) J Org Chem 59:8065

    Article  CAS  Google Scholar 

  516. Burke SD, Piscopio AD, Buchanan JL (1988) Tetrahedron Lett 29:2757

    Article  CAS  Google Scholar 

  517. Burke SD, Piscopio AD, Kort ME, Matulenko MA, Parker MH, Armistead DM, Shankaran K (1994) J Org Chem 59:332

    Article  CAS  Google Scholar 

  518. Burke SD, Armistead DM, Shankaran K (1986) Tetrahedron Lett 27:6295

    Article  CAS  Google Scholar 

  519. Inoue T, Inoue S, Sato K (1990) Bull Chem Soc Jpn 63:1647

    Article  CAS  Google Scholar 

  520. Tietze LF, von Kiedrowski G, Berger B (1982) Angew Chem 94:222 Angew Chem Int Ed Engl 21:221

    Article  CAS  Google Scholar 

  521. Bayles R, Flynn AP, Galt RHB, Kirby S, Turner RW (1988) Tetrahedron Lett 29:6341

    Article  CAS  Google Scholar 

  522. Vogt K, Schmidt RR (1988) Tetrahedron 44:3271

    Article  CAS  Google Scholar 

  523. Pfrengle W, Kunz H (1989) J Org Chem 54:4261

    Article  CAS  Google Scholar 

  524. Kaufman MD, Grieco PA (1994) J Org Chem 59:7197

    Article  CAS  Google Scholar 

  525. Carroll WA, Grieco PA (1993) J Am Chem Soc 115:1164

    Article  CAS  Google Scholar 

  526. Hamada T, Zenkoh T, Sato H, Yonemitsu O (1991) Tetrahedron Lett 32:1649

    Article  CAS  Google Scholar 

  527. Trova MP, McGee, KF Jr (1995) Tetrahedron 51:5951

    Article  CAS  Google Scholar 

  528. Boger DL, Cassidy KC, Nakahara S (1993) J Am Chem Soc. 115:10733

    Article  CAS  Google Scholar 

  529. Boger DL, Hüter O, Mbiya K, Zhang M (1995) J Am Chem Soc 117:11839

    Article  CAS  Google Scholar 

  530. Echavarren AM, Stille JK (1988) J Am Chem Soc 110:4051

    Article  CAS  Google Scholar 

  531. Heathcock CH, Hansen MM, Ruggeri RB, Kath JC (1992) J Org Chem 57:2544; see also: Heathcock CH (1992) Angew Chem 104:675; Angew Chem Int Ed Engl 31:665

    Article  CAS  Google Scholar 

  532. Heathcock CH, Kath JC, Ruggeri RB (1995) J Org Chem 60:1120

    Article  CAS  Google Scholar 

  533. Heathcock CH, Ruggeri RB, McClure KF (1992) J Org Chem 57:2585

    Article  CAS  Google Scholar 

  534. Heathcock CH, Stafford JA, Clark DL (1992) J Org Chem 57:2575

    Article  CAS  Google Scholar 

  535. Heathcock CH, Stafford JA (1992) J Org Chem 57:2566

    Article  CAS  Google Scholar 

  536. Gupta RB, Franck RW (1989) J Am Chem Soc 111:7668

    Article  CAS  Google Scholar 

  537. King SB, Ganem B (1994) J Am Chem Soc 116:562

    Article  CAS  Google Scholar 

  538. Defoin A, Sarazin H, Streith J (1996) Helv Chim Acta 79:560

    Article  CAS  Google Scholar 

  539. Defoin A, Sarazin H, Streith J (1995) Synlett 1187

    Google Scholar 

  540. Hudlicky T, Olivo HF (1991) Tetrahedron Lett 32:6077

    Article  CAS  Google Scholar 

  541. Hudlicky T, Olivo HF (1992) J Am Chem Soc 114:9694

    Article  CAS  Google Scholar 

  542. Martin SF, Tso H-H (1993) Heterocycles 35:85

    Article  CAS  Google Scholar 

  543. Martin SF, Hartmann M, Josey JA (1992) Tetrahedron Lett 33:3583

    Article  CAS  Google Scholar 

  544. Benbow JW, McClure KF, Danishefsky SJ (1993) J Am Chem Soc 115:12305

    Article  CAS  Google Scholar 

  545. McClure KF, Danishefsky SJ (1993) J Am Chem Soc 115:6094

    Article  CAS  Google Scholar 

  546. Benbow JW, Schulte GK, Danishefsky SJ (1992) Angew Chem 104:934; Angew Chem Int Ed Engl 31:915

    Article  CAS  Google Scholar 

  547. McClure KF, Danishefski SJ (1991) J Org Chem 56:850

    Article  CAS  Google Scholar 

  548. Burkholder TP, Fuchs PL (1990) J Am Chem Soc 112:9601

    Article  CAS  Google Scholar 

  549. Keck GE, Romer DR (1993) J Org Chem 58:6083

    Article  CAS  Google Scholar 

  550. Naruse M, Aoyagi S, Kibayashi C (1994) J Org Chem 59:1358

    Article  CAS  Google Scholar 

  551. Shishido Y, Kibayashi C (1992) J Org Chem 57:2876

    Article  CAS  Google Scholar 

  552. Aoyagi S, Shishido Y, Kibayashi C (1991) Tetrahedron Lett 32:4325

    Article  CAS  Google Scholar 

  553. Denmark SE, Thorarensen A, Middleton DS (1995) J Org Chem 60:3574. For a related approach to (-)-hastanecine see: Denmark SE, Thorarensen A (1994) J Org Chem 59:5672

    Article  CAS  Google Scholar 

  554. Vedejs E, Wittenberger SJ (1990) J Am Chem Soc 112:4357

    Article  CAS  Google Scholar 

  555. Vedejs E, Reid JG, Rodgers JD, Wittenberger SJ (1990) J Am Chem Soc 112:4351

    Article  CAS  Google Scholar 

  556. Vedejs E, Rodgers JD, Wittenberger SJ (1988) J Am Chem Soc 110:4822

    Article  CAS  Google Scholar 

  557. Dujardin G, Maudet M, Brown E (1994) Tetrahedron Lett 35:8619

    Article  CAS  Google Scholar 

  558. Jurczak J, Golebiowski A, Raczko J (1988) Tetrahedron Lett 29:5975

    Article  CAS  Google Scholar 

  559. Bauer T, Jurczak J (1992) Polish J Chem 66:1999

    CAS  Google Scholar 

  560. Achmatowicz O, Bialecka-Florianczyk E (1990) Tetrahedron 46:5317

    Article  CAS  Google Scholar 

  561. Vandenput DAL, Scheeren HW (1995) Tetrahedron 51:8383

    Article  CAS  Google Scholar 

  562. Boger DL, Robarge KD (1988) J Org Chem 53:3373

    Article  CAS  Google Scholar 

  563. Tietze LF, Hübsch T, Voss E, Buback M, Tost W (1988) J Am Chem Soc 110:4065

    Article  CAS  Google Scholar 

  564. Buback M, Tost W, Hübsch T, Voss E, Tietze LF (1989) Chem Ber 122:1179

    Article  CAS  Google Scholar 

  565. Tietze LF, Hübsch T, Oelze J, Ott C, Tost W, Wörner G, Buback M (1992) Chem Ber 125:2249

    Article  CAS  Google Scholar 

  566. Buback M, Kuchta G, Niklaus A, Henrich M, Rothert I, Tietze LF (1996) Liebigs Ann 1151

    Google Scholar 

  567. Tietze LF, Hübsch T, Ott C, Kuchta G, Buback M (1995) Liebigs Ann 1

    Google Scholar 

  568. Buback M, Abeln J, Hübsch T, Ott C, Tietze LF (1995) Liebigs Ann 9

    Google Scholar 

  569. Buback M, Gerke K, Ott C, Tietze LF (1994) Chem Ber 127:2241

    Article  CAS  Google Scholar 

  570. Tietze LF, Ott C, Gerke K, Buback M (1993) Angew Chem 105:1536; Angew Chem Int Ed Engl 32, 1485

    Article  CAS  Google Scholar 

  571. Tietze LF, Ott C, Frey U (1996) Liebigs Ann 63

    Google Scholar 

  572. Winter R, Jonas J (1993) High pressure chemistry, biochemistry and materials science. Kluwer, Dordrecht

    Google Scholar 

  573. Matsumoto K, Acheson RM (1991) Organic synthesis at high pressure. Wiley-Interscience, New York

    Google Scholar 

  574. Jurczak J, Baranowski B (1989) High pressure chemical synthesis. Elsevier, Amsterdam

    Google Scholar 

  575. Le Noble WJ (1988) Organic high pressure chemistry. Elsevier, Amsterdam

    Google Scholar 

  576. Isaacs NS (1981) Liquid phase high pressure chemistry. Wiley, Chichester

    Google Scholar 

  577. Isaacs NS (1991) Tetrahedron 47:8463

    Article  CAS  Google Scholar 

  578. Klärner FG (1989) Chem Unserer Zeit 23:53

    Article  Google Scholar 

  579. Van Eldik R, Asano T, le Noble WJ (1989) Chem Rev 89:549

    Article  Google Scholar 

  580. Matsumoto K, Sera A, Uchida T (1985) Synthesis 1

    Google Scholar 

  581. Matsumoto K, Sera A (1985) Synthesis 999

    Google Scholar 

  582. Tietze LF, Hippe T, Steinmetz A (1996) Synlett 1043

    Google Scholar 

  583. Schultz PG, Lerner RA (1995) Science 269:1835.

    Article  CAS  Google Scholar 

  584. Meekel AP, Resmini M, Pandit UK (1995) J Chem Soc Chem Commun:571

    Google Scholar 

  585. Bahr N, Güller R, Reymond JL, Lerner RA (1996) J Am Chem Soc 118:3550

    Article  CAS  Google Scholar 

  586. Review: Lubineau A, Augé J, Queneau Y (1994) Synthesis 741

    Google Scholar 

  587. Review: Li CJ (1993) Chem Rev 93:2023

    Article  CAS  Google Scholar 

  588. Grieco PA, Larsen SD (1985) J Am Chem Soc 107:1768

    Article  Google Scholar 

  589. Grieco PA, Larsen SD, Fobare WF (1986) Tetrahedron Lett 27:1975.

    Article  CAS  Google Scholar 

  590. Wijnen JW, Zavarise S, Engberts JBFN (1996) J Org Chem 61:2001

    Article  CAS  Google Scholar 

  591. Engberts JBFN (1993) Angew Chem 105:1610; Angew Chem Int Ed Engl 32:1545

    Article  Google Scholar 

  592. Lubineau A, Augé J, Grand E, Lubin N (1994) Tetrahedron 50:10265

    Article  CAS  Google Scholar 

  593. Mikami K, Kotera O, Motoyama Y, Sakaguchi H (1995) Synlett 975

    Google Scholar 

  594. Diaz-Ortiz A, Diez-Barra E, de la Hoz A, Prieto P, Moreno A (1994) J Chem Soc Perkin Trans 1:3595

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie der Georg-August Universität, Tammannstr. 2, D-37077, Göttingen, Germany

    Lutz F. Tietze & Georg Kettschau

Authors
  1. Lutz F. Tietze
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Georg Kettschau
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Peter Metz

Rights and permissions

Reprints and permissions

Copyright information

© 1997 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Tietze, L.F., Kettschau, G. (1997). Hetero Diels-Alder reactions in organic chemistry. In: Metz, P. (eds) Stereoselective Heterocyclic Synthesis I. Topics in Current Chemistry, vol 189. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119240

Download citation

  • DOI: https://doi.org/10.1007/BFb0119240

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-62678-7

  • Online ISBN: 978-3-540-68428-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation