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Heterocycles by Cycloadditions of Carbonyl Ylides Generated from Diazo Ketones

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Synthesis of Heterocycles via Cycloadditions I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 12))

Abstract

Carbonyl ylide dipoles are important intermediates with great application in heterocyclic chemistry. Here, we show how the rhodium-catalyzed α-diazocarbonyl compounds are employed in the generation of carbonyl ylides and their effective use for the synthesis, as well as functionalization, of heterocycles. Herein we discuss recent advancements in this field mainly describing the synthesis and importance of various oxygen- and nitrogen-containing heterocyclic systems and natural products from α-diazocarbonyl compounds.

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References

  1. Padwa A, Hornbuckle SH (1991) Chem Rev 91:263

    Article  CAS  Google Scholar 

  2. Maas G (1987) Top Curr Chem 137:75

    CAS  Google Scholar 

  3. Doyle MP (1986) Chem Rev 86:919

    Article  CAS  Google Scholar 

  4. Doyle MP (1986) Acc Chem Res 19:348

    Article  CAS  Google Scholar 

  5. Ye T, McKervey A (1994) Chem Rev 94:1091

    Article  CAS  Google Scholar 

  6. Padwa A (1991) Acc Chem Res 24:22

    Article  CAS  Google Scholar 

  7. Padwa A, Weingarten MD (1996) Chem Rev 96:223

    Article  CAS  Google Scholar 

  8. Padwa A (1997) Top Curr Chem 189:121

    Article  CAS  Google Scholar 

  9. Padwa A (2005) Helv Chim Acta 88:1357

    Article  CAS  Google Scholar 

  10. Padwa A (2005) Organomet Chem 690:5533

    Article  CAS  Google Scholar 

  11. Chiu P (2005) Pure Appl Chem 77:1183

    Article  CAS  Google Scholar 

  12. Mehta G, Muthusamy S (2002) Tetrahedron 58:9477

    Article  CAS  Google Scholar 

  13. Hodgson DM, Pierard FYTM, Stupple PA (2001) Chem Soc Rev 30:50

    Article  CAS  Google Scholar 

  14. Calter MA (1997) Curr Org Chem 1:37

    CAS  Google Scholar 

  15. Padwa A, Krumpe KE (1992) Tetrahedron 48:5385

    Article  CAS  Google Scholar 

  16. McMills MC, Wright D (2002) Chem Heterocycl Compd 59:253

    CAS  Google Scholar 

  17. Karlsson S, Hogberg H-E (2001) Org Prep Proced Int 33:103

    Article  CAS  Google Scholar 

  18. Padwa A (2001) J Organomet Chem 3:617

    Google Scholar 

  19. Nair V, Radhakrishnan KV, Sheela KC (1999) Res Chem Intermed 25:877

    Article  CAS  Google Scholar 

  20. Doyle MP, McKervey MA, Ye T (1998) Modern Catalytic Methods for Organic Syntheis with Diazo Compounds: From Cyclopropanes to Ylides. Wiley-Interscience, New York

    Google Scholar 

  21. Padwa A (ed) (1984) 1,3-Dipolar Cycloaddition Chemistry, Vols 1 and 2. Wiley, New York

    Google Scholar 

  22. Regitz M, Mass G (1986) Aliphatic Diazo Compounds: Properties and Synthesis. Academic Press, New York

    Google Scholar 

  23. Regitz M (ed) (1989) Carbene (Carbenoide): Methoden der Organischen Chemie, Vol. E 19b. Georg Thieme Verlag, New York

    Google Scholar 

  24. Tomioka H (2002) In: Clark JS (ed) Nitrogen, Oxygen and Sulfur Ylide Chemistry. Oxford University Press, Oxford, UK, p 213

    Google Scholar 

  25. Hosomi A, Hojo M, Aihara H (2002) In: Clark JS (ed) Nitrogen, Oxygen and Sulfur Ylide Chemistry. Oxford University Press, Oxford, UK, p 237

    Google Scholar 

  26. Ibata T, Fukushima K (2002) In: Clark JS (ed) Nitrogen, Oxygen and Sulfur Ylide Chemistry. Oxford University Press, Oxford, UK, p 229

    Google Scholar 

  27. Wright DL, McMills MC (2002) In: Clark JS (ed) Nitrogen, Oxygen and Sulfur Ylide Chemistry. Oxford University Press, Oxford, UK, p 218

    Google Scholar 

  28. Whiting DA (1995) In: Katrizky AR, Meth-Cohn O, Rees CW (eds) Comprehensive Organic Functional Group Transformations. Elsevier, Oxford, UK, pp 3, 313 and 733

    Google Scholar 

  29. McMills MC, Wright D (2003) In: Padwa A, Pearson WH (eds) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Chap 4. Wiley, Hoboken, p 253

    Google Scholar 

  30. Padwa A (ed) (1984) 1,3-Dipolar Cycloaddition Chemistry, Vol 1. Wiley, New York, pp 1–176

    Google Scholar 

  31. Takebayashi M, Ibata T, Ueda K (1970) Bull Chem Soc Jpn 43:1500

    Article  CAS  Google Scholar 

  32. Paulissen R, Reimlinger H, Hayez A, Hubert AJ, Teyssié PH (1973) Tetrahedron Lett 3:2233

    Article  Google Scholar 

  33. Linn WJ, Benson RE (1965) J Am Chem Soc 87:3657

    Article  Google Scholar 

  34. Ruf SG, Bergstrasser U, Regitz M (2000) Eur J Org Chem, p 2219

    Google Scholar 

  35. Bhattacharyya K, Das PK (1999) Res Chem Intermed 25:645

    Article  CAS  Google Scholar 

  36. Kotera M, Ishii K, Hiraga M, Sakamoto M (1999) Heterocycles 51:2147

    Article  CAS  Google Scholar 

  37. Matsumoto K, Taketsuna H, Ikemi Y, Kakehi A, Uchida T, Otani S (1998) Heterocycles 49:79

    Article  CAS  Google Scholar 

  38. Das PK, Griffin GW (1984) J Photochem 27:317

    Article  CAS  Google Scholar 

  39. Huisgen R (1977) Angew Chem Int Ed Engl 16:572

    Article  Google Scholar 

  40. Merkley N, El-Saidi M, Warkentin (2000) Can J Chem 78:356

    Google Scholar 

  41. Couture P, Warkentin (1997) Can J Chem 75:1264

    Google Scholar 

  42. Couture P, El-Saidi M, Warkentin (1997) Can J Chem 75:326

    Google Scholar 

  43. lliott GI, Velcicky J, Ishikawa H, Li Y, Boger DL (2006) Angew Chem Int Ed 45:620

    Article  CAS  Google Scholar 

  44. Keus D, Kaminski M, Warkentin JJ (1984) Org Chem 49:343

    Article  CAS  Google Scholar 

  45. Bèkhazi M, Warkentin JJ (1983) Am Chem Soc 105:1289

    Article  Google Scholar 

  46. Friedman LA, Sabat M, Harman WD (2002) J Am Chem Soc 124:7395

    Article  CAS  Google Scholar 

  47. Snider BB, Wu X, Nakamura S, Hashimoto S (2007) Org Lett 9:873

    Article  CAS  Google Scholar 

  48. Tomioka H (1998) Bull Chem Soc Jpn 71:1501

    Article  CAS  Google Scholar 

  49. De March P, Huisgen RJ (1982) Am Chem Soc 104:4952

    Article  Google Scholar 

  50. Alt M, Mass G (1994) Tetrahedron 50:7435

    Article  CAS  Google Scholar 

  51. Johnson T, Cheshire DR, Stocks MJ, Thurston VT (2001) Synlett, p 646

    Google Scholar 

  52. Alt M, Maas G (1994) Chem Ber 127:1537

    Article  CAS  Google Scholar 

  53. Doyle MP, Forbes DC, Protopopova MN, Stanley SA, Vasbinder MM, Xavier KR (1997) J Org Chem 62:7210

    Article  CAS  Google Scholar 

  54. Ibata T, Motoyama T, Hamaguchi (1976) M Bull Chem Soc Jpn 49:2298

    Google Scholar 

  55. Hodgson DM, Stupple PA, Pierard FYTM, Labande AH, Johnstone C (2001) Chem Eur J 7:4465

    Article  CAS  Google Scholar 

  56. Hodgson DM, Avery TD, Donohue AC (2002) Org Lett 4:1809

    Article  CAS  Google Scholar 

  57. Hodgson DM, Glen R, Redgrave AJ (2002) Tetrahedron Lett 43:3927

    Article  CAS  Google Scholar 

  58. Hodgson DM, Labande AH, Pierard FYTM, Castro MÁE (2003) J Org Chem 68:6153

    Article  CAS  Google Scholar 

  59. Hodgson DM, Selden DA, Dossetter AG (2003) Tetrahedron Asymmetry 14:3841

    Article  CAS  Google Scholar 

  60. Hodgson DM, Labande AH, Pierard FYTM (2003) Synlett, p 59

    Google Scholar 

  61. Hodgson DM, Glen R, Grant GH, Redgrave AJ (2003) J Org Chem 68:581

    Article  CAS  Google Scholar 

  62. Hodgson DM, Stupple PA, Johnstone C (2003) Arkivoc 7:49

    Google Scholar 

  63. Hodgson DM, Labande AH, Glen R, Redgrave AJ (2003) Tetrahedron Asymmetry 14:921

    Article  CAS  Google Scholar 

  64. Snyder JP, Padwa A, Stengel T, Arduengo AJ III, Jockisch A, Kim H-J (2001) J Am Chem Soc 123:11318

    Article  CAS  Google Scholar 

  65. Johnson T, Cheshire DR, Stocks MJ, Thurston VT (2001) Synlett, p 646

    Google Scholar 

  66. Nair JS, Mathai S, Varma RL (2004) J Org Chem 69:1413

    Article  CAS  Google Scholar 

  67. Hamaguchi M, Matsubara H, Nagai T (2000) Tetrahedron Lett 41:1457

    Article  CAS  Google Scholar 

  68. Lu C-D, Chen Z-Y, Liu H, Hu WH, Mi AQ, Doyle MP (2004) J Org Chem 69:4856

    Article  CAS  Google Scholar 

  69. Muthusamy S, Gunanathan C, Nethaji M (2004) J Org Chem 69:5631

    Article  CAS  Google Scholar 

  70. Muthusamy S, Gunanathan C, Nethaji M (2004) Synlett, p 639

    Google Scholar 

  71. Jiang B, Zhang X, Luo Z (2002) Org Lett 4:2453

    Article  CAS  Google Scholar 

  72. Lu C-D, Chen Z-Y, Liu H, Hu WH, Mi AQ (2004) Org Lett 6:3071

    Article  CAS  Google Scholar 

  73. Russell AE, Brekan J, Gronenberg L, Doyle MP (2004) J Org Chem 69:5269

    Article  CAS  Google Scholar 

  74. Nair JS, Mathai S, Mathew SC, Rath NP (2005) Tetrahedron 61:2849

    Article  CAS  Google Scholar 

  75. Torssell S, Kienle M, Somfai P (2005) Angew Chem Int Ed 44:3096

    Article  CAS  Google Scholar 

  76. Torssell S, Somfai P (2006) Adv Synth Catal 348:2421

    Article  CAS  Google Scholar 

  77. Liebman JF, Greenberg A (1976) Chem Rev 76:311

    Article  CAS  Google Scholar 

  78. Padwa A, Sandanayaka VP, Curtis EA (1994) J Am Chem Soc 116:2667

    Article  CAS  Google Scholar 

  79. Padwa A, Curtis EA, Sandanayaka VP (1996) J Org Chem 61:73

    Article  CAS  Google Scholar 

  80. Molchanov AP, Diev VV, Magull J, Vidovic D, Kozhushkov SI, De Meijere A, Kostikov RR (2005) Eur J Org Chem 593

    Google Scholar 

  81. Nair V, Rajesh C, Dhanya R, Vinod AU (2001) Tetrahedron Lett 42:2045

    Article  CAS  Google Scholar 

  82. Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P, Jasra RV (2000) Tetrahedron 56:6307

    Article  CAS  Google Scholar 

  83. Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P (2001) Synlett, p 1407

    Google Scholar 

  84. Muthusamy S, Babu SA, Gunanathan C (2002) Tetrahedron Lett 43:5981

    Article  CAS  Google Scholar 

  85. Muthusamy S, Gnanaprakasam B (2007) Tetrahedron 63:3355

    Article  CAS  Google Scholar 

  86. Muthusamy S, Gunanathan C, Babu SA (2001) Tetrahedron Lett 42:523

    Article  CAS  Google Scholar 

  87. Muthusamy S, Gunanathan C, Suresh E (2004) Tetrahedron 60:7885

    Article  CAS  Google Scholar 

  88. Muthusamy S, Krishnamurthi J, Nethaji MJ (2005) Chem Soc Chem Commun, p 3862

    Google Scholar 

  89. Padwa A, Zhang ZJ, Zhi LJ (2000) Org Chem 65:5223

    Article  CAS  Google Scholar 

  90. Wood JL, Thompson BD, Yusuff N, Pflum DA, Matthäus MSP (2001) J Am Chem Soc 123:2097

    Article  CAS  Google Scholar 

  91. Nakanishi K, Tada M, Yamada Y, Ohashi M, Komatsu N, Terakawa H (1963) Nature 197:292

    Article  CAS  Google Scholar 

  92. French AL, Garrettson LK (1988) Clin Toxicol 26:81

    Article  CAS  Google Scholar 

  93. Kinder FR Jr, Bair KW (1994) J Org Chem 59:6965

    Article  CAS  Google Scholar 

  94. Padwa A, Curtis EA, Sandanayaka VP (1997) J Org Chem 62:1317

    Article  CAS  Google Scholar 

  95. McMorris TC, Yu J, Hu Y (1997) J Org Chem 62:3015

    Article  CAS  Google Scholar 

  96. Padwa A (1997) Farmaco 52:303

    CAS  Google Scholar 

  97. Pirrung MC, Liu H (2003) Org Lett 5:1983

    Article  CAS  Google Scholar 

  98. McMorris TC, Cong Q, Kelner MJ (2003) J Org Chem 68:9648

    Article  CAS  Google Scholar 

  99. McMorris TC, Staake MD, Kelner MJ (2004) J Org Chem 69:619

    Article  CAS  Google Scholar 

  100. Diev VV, Kostikov RR, Gleiter R, Molchanov AP (2006) J Org Chem 71:4066

    Article  CAS  Google Scholar 

  101. Nair V, Sethumadhavan D, Sheela KC, Nair SM, Eigendorf GK (2002) Tetrahedron 58:3009

    Article  CAS  Google Scholar 

  102. Hodgson DM, Angrish D, Labande AH (2006) Chem Commun, p 627

    Google Scholar 

  103. Hodgson DM, Angrish D (2006) Adv Synth Catal 348:2509

    Article  CAS  Google Scholar 

  104. Suga H, Ishida H, Ibata T (1998) Tetrahedron Lett 39:3165

    Article  CAS  Google Scholar 

  105. Kanemasa S, Uemura T, Wada E (1992) Tetrahedron Lett 33:7889

    Article  CAS  Google Scholar 

  106. Gothelf KV, Thomsen I, Jorgensen KA (1996) J Am Chem Soc 118:59

    Article  CAS  Google Scholar 

  107. Hodgson DM, Stupple PA, Johnstone C (1997) Tetrahedron Lett 38:6471

    Article  CAS  Google Scholar 

  108. Padwa A, Hornbuckle SF, Fryxell GE, Zhang ZJ (1992) J Org Chem 57:5747

    Article  CAS  Google Scholar 

  109. Hodgson DM, Stupple PA, Johnstone C (1999) Chem Commun, p 2185

    Google Scholar 

  110. Kitagaki S, Yasugahira M, Anada M, Nakajima M, Hashimoto S (2000) Tetrahedron Lett 41:5931

    Article  CAS  Google Scholar 

  111. Kitagaki S, Anada M, Kataoka O, Matsuno K, Umeda C, Watanabe N, Hashimoto S-I (1999) J Am Chem Soc 121:1417

    Article  CAS  Google Scholar 

  112. Hashimoto S-I, Watanabe N, Sato T, Shiro M, Ikegami S (1993) Tetrahedron Lett 34:5109

    Article  CAS  Google Scholar 

  113. Garcia Ruano JL, Fraile A, Rosario Martin M, Nunez A (2006) J Org Chem 71:6536

    Article  CAS  Google Scholar 

  114. Friedrichsen W, Plug C (1992) Tetrahedron Lett 33:7509

    Article  Google Scholar 

  115. Baldwin JE, Mayweg AVW, Neumann K, Pritchard GJ (1999) Org Lett 1:1933

    Article  CAS  Google Scholar 

  116. Padwa A, Precedo L, Semones MA (1999) J Org Chem 64:4079

    Article  CAS  Google Scholar 

  117. Padwa A, Boonsombat J, Rashatasakhon P, Willis J (2005) Org Lett 7:3725

    Article  CAS  Google Scholar 

  118. Chiu P, Chen B, Cheng KF (2001) Org Lett 3:1721

    Article  CAS  Google Scholar 

  119. Chen B, Ko RYY, Yuen MSM, Cheng K-F, Chiu P (2003) J Org Chem 68:4195

    Article  CAS  Google Scholar 

  120. Geng Z, Chen B, Chiu P (2006) Angew Chem Int Ed 45:6197

    Article  CAS  Google Scholar 

  121. Nakamura S, Sugano Y, Kikuchi F, Hashimoto S (2006) Angew Chem Int Ed 45:6532

    Article  CAS  Google Scholar 

  122. Hodgson DM, Le Strat F, Avery TD, Donohue AC, Brückl T (2004) J Org Chem 69:8796

    Article  CAS  Google Scholar 

  123. Hodgson DM, Le Strat F (2004) J Chem Soc Chem Commun, p 822

    Google Scholar 

  124. Graening T, Bette V, Neudorfl J, Lex J, Schmalz H-G (2005) Org Lett 7:4317

    Article  CAS  Google Scholar 

  125. Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P (2001) Bull Chem Soc Jpn 75:801

    Article  Google Scholar 

  126. Muthusamy S, Babu SA, Gunanathan C, Ganguly B, Suresh E, Dastidar P (2002) J Org Chem 67:8019

    Article  CAS  Google Scholar 

  127. Muthusamy S, Krishnamurthi J, Nethaji (2004) Tetrahedron Lett 45:6485

    Google Scholar 

  128. Muthusamy S, Krishnamurthi J, Suresh E (2005) Arkivoc xi:146

    Google Scholar 

  129. Padwa A, Fryxell GE, Zhi L (1990) J Am Chem Soc 112:3100

    Article  CAS  Google Scholar 

  130. Muthusamy S, Babu SA, Gunanathan C (2000) Tetrahedron Lett 41:8839

    Article  CAS  Google Scholar 

  131. Muthusamy S, Krishnamurthi J, Babu SA, Suresh E (2007) J Org Chem 72:1252

    Article  CAS  Google Scholar 

  132. Pirrung MC, Kaliappan KP (2000) Org Lett 2:353

    Article  CAS  Google Scholar 

  133. Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P, Jasra RV (2001) Tetrahedron 57:7009

    Article  CAS  Google Scholar 

  134. Nair V, Sheela KC, Sethumadhavan D, Bindu S, Rath NR, Eigendorf GK (2001) Synlett, p 272

    Google Scholar 

  135. Muthusamy S, Babu SA, Nethaji M (2003) Tetrahedron 59:8117

    Article  CAS  Google Scholar 

  136. Winkler JD, Mikochic PJ (2004) Org Lett 6:3735

    Article  CAS  Google Scholar 

  137. Suga H, Kakehi A, Ito S, Inoue K, Ishida H, Ibata T (2000) Org Lett 2:3145

    Article  CAS  Google Scholar 

  138. Suga H, Inoue K, Inoue S, Kakehi A (2002) J Am Chem Soc 124:14836

    Article  CAS  Google Scholar 

  139. Suga H, Inoue K, Inoue S, Kakehi A, Shiro M (2005) J Org Chem 70:47

    Article  CAS  Google Scholar 

  140. Tsutsui H, Shimada N, Abe T, Anada M, Nakajima M, Nakamura S, Nambu H, Hashimoto S (2007) Adv Synth Catal 349:521

    Article  CAS  Google Scholar 

  141. Koyama H, Ball RG, Berger GD (1994) Tetrahedron Lett 35:9185

    Article  CAS  Google Scholar 

  142. Hodgson DM, Bailey JM, Villalonga-Barber C, Drew MGB, Harrison T (2000) J Chem Soc Perkin Trans 1, p 3432

    Google Scholar 

  143. Kataoka O, Kitagaki S, Watanabe N, Kobayashi J, Nakamura S, Shiro M, Hashimoto S (1998) Tetrahedron Lett 39:2371

    Article  CAS  Google Scholar 

  144. Nakamura S, Hirata Y, Kurosaki T, Anada M, Kataoka O, Kitagaki S, Hashimoto S (2003) Angew Chem Int Ed Engl 42:5351

    Article  CAS  Google Scholar 

  145. Hirata Y, Nakamura S, Watanabe N, Kataoka O, Kurosaki T, Anada M, Kitagaki S, Shiro M, Hashimoto S (2006) Chem Eur J 12:8898

    Article  CAS  Google Scholar 

  146. Muthusamy S, Krishnamurthi J, Suresh E (2005) Synlett, p 3002

    Google Scholar 

  147. Muthusamy S, Krishnamurthi J, Suresh E (2006) Org Lett 8:5101

    Article  CAS  Google Scholar 

  148. Suga H, Ebiura Y, Fukushima K, Kakehi A, Baba T (2005) J Org Chem 70:10782

    Article  CAS  Google Scholar 

  149. Hamaguchi M, Ibata T (1974) Tetrahedron Lett, p 4475

    Google Scholar 

  150. Maier ME, Evertz K (1988) Tetrahedron Lett, p 1677

    Google Scholar 

  151. Hertzog DL, Austin DJ, Nadler WR, Padwa A (1992) Tetrahedron Lett 33:4731

    Article  CAS  Google Scholar 

  152. Osterhaut MH, Nadler WR, Padwa A (1994) Synthesis, p 123

    Google Scholar 

  153. Savinov SN, Austin DJ (1999) J Chem Soc Chem Commun, p 1813

    Google Scholar 

  154. Ruf SF, Bergsträßer U, Regitz M (2000) Tetrahedron 56:63

    Article  CAS  Google Scholar 

  155. Looper RE, Pizzirani D, Schreiber L (2006) Org Lett 8:2063

    Article  CAS  Google Scholar 

  156. Padwa A, Brodney MA, Marino JP Jr, Osterhout MH, Price AT (1997) J Org Chem 62:67

    Article  CAS  Google Scholar 

  157. Brodney MA, Padwa A (1999) J Org Chem 64:556

    Article  CAS  Google Scholar 

  158. Liu F, Austin DJ (2001) Org Lett 3:2273

    Article  CAS  Google Scholar 

  159. Rovnyak GC, Kimball SD, Beyer B, Cucinotta G, DiMarco JD, Gougoutas J, Hedberg A, Malley M, McCarthy JP, Zhang R, Moreland S (1995) J Med Chem 38:119

    Article  CAS  Google Scholar 

  160. Jauk B, Belaj F, Kappe CO (1999) J Chem Soc Perkin Trans 1, p 307

    Google Scholar 

  161. Savinov SN, Austin DJ (2002) Org Lett 4:1415

    Article  CAS  Google Scholar 

  162. Savinov SN, Austin DJ (2002) Org Lett 4:1419

    Article  CAS  Google Scholar 

  163. Padwa A, Prein M (1998) Tetrahedron 54:6957

    Article  CAS  Google Scholar 

  164. Zhang X, Schmitt AC, Decicco CP (2002) Tetrahedron Lett 43:9663

    Article  CAS  Google Scholar 

  165. Hong X, France S, Padwa A (2007) Tetrahedron 63:5962

    Article  CAS  Google Scholar 

  166. Hong X, France S, Mejia-Oneto JM, Padwa A (2006) Org Lett 8:5141

    Article  CAS  Google Scholar 

  167. Padwa A, Harring SR, Semones MA (1998) J Org Chem 63:44

    Article  CAS  Google Scholar 

  168. Heathcock CH, Norman MH, Dickman DA (1990) J Org Chem 55:798

    Article  CAS  Google Scholar 

  169. Padwa A, Price AT (1995) J Org Chem 60:6258

    Article  CAS  Google Scholar 

  170. Mejia-Oneto JM, Padwa A (2006) Org Lett 8:3275

    Article  CAS  Google Scholar 

  171. England DB, Padwa A (2007) Org Lett 9:3249

    Article  CAS  Google Scholar 

  172. Padwa A, Hasegawa T, Liu B, Zhang Z (2000) J Org Chem 65:7124

    Article  CAS  Google Scholar 

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Alfred Hassner

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Muthusamy, S., Krishnamurthi, J. (2008). Heterocycles by Cycloadditions of Carbonyl Ylides Generated from Diazo Ketones. In: Hassner, A. (eds) Synthesis of Heterocycles via Cycloadditions I. Topics in Heterocyclic Chemistry, vol 12. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2007_098

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