Highly diastereoselective radical addition to glyoxylic oxime ether: asymmetric synthesis of α-amino acids

Abstract

A high degree of stereocontrol in radical addition to the Oppolzer’s camphor sultam derivative of glyoxylic oxime ether was achieved, providing a convenient method for preparing a variety of enantiomerically pure α-amino acids.

References

1. D. P. Curran, N. A. Porter and B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996For recent reviews: W. Smadja, Synlett, 1994, 1; N. A. Porter, B. Giese and D. P. Curran, Acc. Chem. Res., 1991, 24, 296.
2. S. E. Booth, P. R. Jenkins, C. J. Swain and J. B. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1994, 3499.
3. For some recent examples: D. L. J. Clive and J. Zhang, Chem. Commun., 1997, 549; J. Marco-Contelles, G. Balme, D. Bouyssi, C. Destabel, C. D. Henriet-Bernard, J. Grimaldi and J. M. Hatem, J. Org. Chem., 1997, 62, 1202; G. E. Keck and T. T. Wager, J. Org. Chem., 1996, 61, 8366; G. J. Hollingworth, G. Pattenden and D. J. Schulz, Aust. J. Chem., 1995, 48, 381; J. L. Chiara, J. Marco-Contelles, N. Khiar, P. Gallego, C. Destabel and M. Bernabé, J. Org. Chem., 1995, 60, 6010; M. Santagostino and J. D. Kilburn, Tetrahedron Lett., 1995, 36, 1365; J. W. Grissom and D. Klingberg, J. Org. Chem., 1994, 59, 7876; K. A. Parker and D. Fokas, J. Org. Chem., 1994, 59, 3927; T. Naito, K. Tajiri, T. Harimoto, I. Ninomiya and T. Kiguchi, Tetrahedron Lett., 1994, 35, 2205; E. W. Della and A. M. Knill, Aust. J. Chem., 1994, 47, 1833.
4. B. Bhat, E. E. Swayze, P. Wheeler, S. Dimock, M. Perbost and Y. S. Sanghvi, J. Org. Chem., 1996, 61, 8186; S. Kim, I. Y. Lee, J.-Y. Yoon and D. H. Oh, J. Am. Chem. Soc., 1996, 118, 5138; D. J. Hart and F. L. Seely, J. Am. Chem. Soc., 1988, 110, 1631.
5. S. Hanessian and R.-Y. Yang, Tetrahedron Lett., 1996, 37, 5273.
6. Y. Yamamoto and W. Ito, Tetrahedron, 1988, 44, 5415; J.-C. Fiaud and H. B. Kagan, Tetrahedron Lett., 1970, 1813.
7. S. Cicchi, A. Goti, A. Brandi, A. Guarna and F. De Sarlo, Tetrahedron Lett., 1990, 31, 3351; M. Nitta and T. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1985, 1401.
8. W. Oppolzer, O. Tamura and J. Deerberg, Helv. Chim. Acta, 1992, 75, 1965.
9. N. Risch and M. Arend, Stereoselective Synthesis, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme, Stuttugart, New York 1966, vol. 3, p. 1876; R. A. Volkmann, Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford 1991, vol. 1, p. 355.