Stereo-divergent synthesis of L-threo- and L-erythro-[2,3-2H2]amino acids using optically active dioxopiperazine as a chiral template

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 7, 1998, Pages 1275-1281

  Oba, Makoto ^a   Terauchi, Tsutomu ^a   Qwari, Yuki ^a   Imai, Yoko ^b   Motoyama, Izumi ^b   Nishiyama, Kozaburo ^a  

^a TOKAI UNIVERSITY   (Japan)

^b KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748823448     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708412i     Document Type: Article

References (21)

1. K. Wuthrich, NMR of Proteins and Nucleic Acids, Wiley, New York, 1986;
2. G. C. K. Roberts, NMR of Macromolecules. A Practical Approach, Oxford University Press, Oxford, 1993.
3. Our recent work, see: (a) M. Oba and K. Nishiyama, Tetrahedron, 1994, 50, 10 193;
4. (b) K. Nishiyama, M. Oba, R. Ueno, A. Morita, Y. Nakamura and M. Kainosho, J. Labelled Compd. Radiopharm., 1994, 34, 831;
5. (c) M. Oba, T. Terauchi, J. Hashimoto, T. Tanaka and K. Nishiyama, Tetrahedron Lett., 1997, 38, 5515.
6. M. Oba, R. Ueno, M. Fukuoka, M. Kainosho and K. Nishiyama, J. Chem. Soc., Perkin Trans. 1, 1995, 1603.
7. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, 1989.
8. M. Oba, S. Nakajima and K. Nishiyama, Chem. Commun., 1996, 1875.
9. A catalytic hydrogenation of dehydrodioxopiperazine derivatives has been reported by Izumiya et al., however, it was limited to non-protected dioxopiperazine derivatives and the chief chiral auxiliary employed for their work was L-alanine, see: (a) T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Tetrahedron Lett., 1979, 4483;
10. (b) S. Lee, T. Kanmera, H. Aoyagi and N. Izumiya, Int. J. Peptide Protein Res., 1979, 13, 207;
11. (c) T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, int. J. Peptide Protein Res., 1980, 16, 280;
12. (d) K. Tanimura, T. Kato, M. Waki, S. Lee, Y. Kodera and N. Izumiya, Bull. Chem. Soc. Jpn., 1984, 57, 2193.
13. C. Gallina and A. Liberatori, Tetrahedron, 1974, 30, 667.
14. M. M. Campbell, D. C. Horwell, M. F. Mahon, M. C. Pritchard and S. P. Walfold, Bioorg. Med. Chem. Lett., 1993, 3, 667.
15. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1987, 107, 3902.
16. M. Oba, Y. Kawahara, K. Nishiyama, M. Kitsukawa and M. Kainosho, Bulletin of the School of High-Technology for Human Welfare Tokai University, 1994, 3, 125.
17. J. E. Rose, P. D. Leeson and D. Gani, J. Chem. Soc., Perkin Trans. 1, 1992, 1563.
18. G. M. Sheldrick, Crystallographic Computing 3, Oxford University Press, Oxford, 1985.
19. D. T. Cromer and J. T. Waber, International Tables for X-ray Crystallography, The Kynoch Press, Birmingham, UK, 1974, vol. IV, Table 2.2 A.
20. J. A. Ibers and W. C. Hamilton, Acta Crystallogr., 1964, 17, 781.
21. D. C. Creagh and W. J. McAuley, International Tables for Crystallography, Kluwer Academic Publishers, Boston, 1992, vol. C, Table 4.2.6.8.