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7 References
Rando, R. R.: Acc. Chem. Res. 8, 281 (1975); Abeles, R. H., Maycock, A. L.: ibid. 9, 313 (1976); Abeles, R. H.: Pure & Appl. Chem. 53, 149 (1980); Trowitzsch, W., Sahm, H.: Z. Naturforsch., Teil C 32, 78 (1977)
Nass, G., Poralla, K., Zähner, H.: Naturwissenschaften 58, 603 (1971)
Bell, E. A.: Endeavour 4, 102 (1980)
Recent reviews on asymmetric synthesis, including amino acids ApSimon, J. W., Seguin, R. P.: Tetrahedron 35, 2797 (1979); Weinges, K., Stemmle, B.: Recent Develop. Chem. Nat. Carbon Compd. 7, 91 (1976); Valentine jr., D., Scott, J. W.: Synthesis 1978, 329; Kagan, H. B.: Pure & Appl. Chem. 43, 401 (1975)
Morrison, J. D., Mosher, H. S.: Asymmetric Organic Reactions, 1. Aufl., Prentice Hall, Englewood Cliffs 1971
Schöllkopf, U. et al.: Angew. Chem. 90, 136 (1978); Angew. Chem. Int. Ed. Engl. 17, 117 (1978); Schöllkopf, U. et al.: Liebigs Ann. Chem. 1981, 439
Cf. Pankaskie, M., Abdel-Monem, M.: J. Med. Chem. 23, 121 (1980)
Jung, G., Brückner, H., Schmitt, H.: in (Voelter, W., Weitzel, G., Eds.) Structure and Activity of Natural Peptides, 1981, 75, Walter de Gruyter, Berlin 1981
Schöllkopf, U. et al.: Liebigs Ann. Chem. 1981, 696
Cf. Blake, K. W., Porter, A. E. A., Sammes, P. G.: J. Chem. Soc. Perkin I 1972, 2494
Cf. Schmidt, R. R.: Angew. Chem. 87, 603 (1975); Angew. Chem. Int. Ed. Engl. 14, 581 (1975)
Weinges, K. et al.: Chem. Ber. 104, 3594 (1971). See this paper for alternative asymmetric syntheses of α-methyl amino acids as well as Kolb, M., Barth, J.: Tetrahedron Lett. 1979, 2999; Suzuki, M. et al.: Chem. Ind. (London) 1972, 687
Schöllkopf, U., Groth, U., Hartwig, W.: Liebigs Ann. Chem. 1981, 2407
This alternative model is analogous to the one proposed for the aldol addition. Cf. Kleschick, W. A., Buse, C. T., Heathcock, C. H.: J. Am. Chem. Soc. 99, 247 (1977); Buse, C. T., Heathcock, C. H.: ibid. 99, 8109 (1977); Fellmann, P., Dubois, J.-E.: Tetrahedron 34, 1349 (1978); House, H. O., Crumrine, D. S., Teranishi, A. Y., Olmstead, H. D.: J. Am. Chem. Soc. 95, 3310 (1973). Very likely, in the “real” transition state both factors, (HOMO)-LUMO) attraction and lithium complexation play a role.
Schöllkopf, U. et al.: Synthesis 1981, 969. For an alternative synthesis of amino acids NCAs with trichlormethyl chloroformate instead of phosgene cf. Oya, M., Katakai, R., Nakai, H.: Chem. Lett. 1973, 1143
Schöllkopf, U., Groth, U., Deng, C.: Angew. Chem. 93, 793 (1981), Angew. Chem. Int. Ed. Engl. 20, 798 (1981)
Groth, U.: Dissertation, Univ. of Göttingen 1981
Schöllkopf, U., Neubauer, J.: Synthesis 1982, 861
Schöllkopf, U. et al.: Synthesis 1981, 966
Kehne, H.: Dissertation, Univ. of Göttingen 1980
Dauben, W. G., Fonken, G. J., Noyce, D. S.: J. Am. Chem. Soc. 78, 2579 (1956)
Lonsky, R.: Diplomarbeit, Univ. of Göttingen 1980
Groth, U., Schöllkopf, U., Chiang, Y.: Synthesis 1982, 864
Westphalen, K.-O.: Dissertation, Univ. of Göttingen, presumably 1983
Nozulak, J.: Dissertation, Univ. of Göttingen, presumably 1983
We recently learned, that tert-leucine can in fact be obtained in almost optically pure form by enzymatic resolution. Sauber, K.: Hoechst AG, Pharmaforschung, private communication
Cf. argumentation in ref. 13)
Schöllkopf, U., Groth, U.: Angew. Chem. 93, 1022 (1981); Angew. Chem. Int. Ed. Engl. 20, 977 (1981)
Chari, R. V. J., Wemple, J.: Tetrahedron Lett. 1979, 111
Schöllkopf, U., Nozulak, J., Groth, U.: Synthesis 1982, 868; this paper also describes the synthesis of 49 from 37a
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Schöllkopf, U. (1983). Enantioselective synthesis of nonproteinogenic amino acids. In: Wittig Chemistry. Topics in Current Chemistry, vol 109. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0018056
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