Substituent-dependent asymmetric synthesis of L-threo- and L-erythro-[2,3-2H2]phenylalanine from chiral (Z)-dehydrophenylalanine

Chemical Communications

Volumn , Issue 16, 1996, Pages 1875-1876

  Oba, Makoto ^a   Nakajima, Shinji ^a   Nishiyama, Kozaburo ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004420420     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001875     Document Type: Article

References (11)

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2. K. Wuthrich, NMR of Proteins and Nucleic Acids, Wiley, New York, 1986; G. C. K. Roberts, NMR of Macromolecules. A Practical Approach, Oxford University Press, Oxford, 1993.
3. M. Oba, R. Ueno, M. Fukuoka, M. Kainosho and K. Nishiyama J. Chem. Soc., Perkin Trans. 1, 1995, 1603.
4. A catalytic hydrogenation of dehydrodiketopiperadine derivatives as reported by Izumiya and coworkers, however, it was limited to non-protected diketopiperazine derivatives and the chief chiral auxiliary employed for their works was L-alanine, see: T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Tetrahedron Lett., 1979, 4483; S. Lee, T. Kanmera, H. Aoyagi and N. Izumiya, Int. J. Pept. Protein Res., 1979, 13, 207; T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Int. J. Pept; Protein Res., 1980, 16, 280; K. Tanimura, T. Kato, M. Waki, S. Lee, Y. Kodera and N. Izumiya, Bull. Chem. Soc. Jpn., 1984, 57, 2193.
5. A catalytic hydrogenation of dehydrodiketopiperadine derivatives as reported by Izumiya and coworkers, however, it was limited to non-protected diketopiperazine derivatives and the chief chiral auxiliary employed for their works was L-alanine, see: T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Tetrahedron Lett., 1979, 4483; S. Lee, T. Kanmera, H. Aoyagi and N. Izumiya, Int. J. Pept. Protein Res., 1979, 13, 207; T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Int. J. Pept; Protein Res., 1980, 16, 280; K. Tanimura, T. Kato, M. Waki, S. Lee, Y. Kodera and N. Izumiya, Bull. Chem. Soc. Jpn., 1984, 57, 2193.
6. A catalytic hydrogenation of dehydrodiketopiperadine derivatives as reported by Izumiya and coworkers, however, it was limited to non-protected diketopiperazine derivatives and the chief chiral auxiliary employed for their works was L-alanine, see: T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Tetrahedron Lett., 1979, 4483; S. Lee, T. Kanmera, H. Aoyagi and N. Izumiya, Int. J. Pept. Protein Res., 1979, 13, 207; T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Int. J. Pept; Protein Res., 1980, 16, 280; K. Tanimura, T. Kato, M. Waki, S. Lee, Y. Kodera and N. Izumiya, Bull. Chem. Soc. Jpn., 1984, 57, 2193.
7. A catalytic hydrogenation of dehydrodiketopiperadine derivatives as reported by Izumiya and coworkers, however, it was limited to non-protected diketopiperazine derivatives and the chief chiral auxiliary employed for their works was L-alanine, see: T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Tetrahedron Lett., 1979, 4483; S. Lee, T. Kanmera, H. Aoyagi and N. Izumiya, Int. J. Pept. Protein Res., 1979, 13, 207; T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Int. J. Pept; Protein Res., 1980, 16, 280; K. Tanimura, T. Kato, M. Waki, S. Lee, Y. Kodera and N. Izumiya, Bull. Chem. Soc. Jpn., 1984, 57, 2193.
8. J. E. Rose, P. D. Leeson and D. Gani, J. Chem. Soc., Perkin Trans. 1, 1992, 1563.
9. C. Gallina and A. Liberatori, Tetrahedron, 1974, 30, 667.
10. S. Moor and W. H. Stein, J. Biol. Chem., 1951, 192, 663.
11. M. Oba, Y. Kawahara, K. Nishiyama, M. Kitsukawa and M. Kainoshi, The Bulletin of School of High-Technology for Human Welfare, Tokai University, 1994, vol. 3, pp. 125.