Reductive deamination of α-amino carbonyl compounds by means of samarium iodide

Chemical Communications

Volumn , Issue 12, 1999, Pages 1065-1066

  Honda, Toshio ^a   Ishikawa, Fumihiro ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBONYL DERIVATIVE; IODIDE; NITROGEN; SAMARIUM;

ARTICLE; DEAMINATION; REACTION TIME;

EID: 0033591752     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903073e     Document Type: Article

References (32)

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19. T. Honda, S. Yamane, K. Naito, K. and Y. Suzuki, Heterocycles, 1994, 37, 515; T. Honda, F. Ishikawa and S. Yamane, J. Chem. Soc., Chem. Commun., 1994, 499; T. Honda, S. Yamane, K. Naito and Y. Suzuki, Heterocycles, 1995, 40, 301; T. Honda, F. Ishikawa and S. Yamane, J. Chem. Soc., Perkin Trans. 1, 1996, 1125; T. Honda, S. Yamane, F. Ishikawa and M. Katoh, Tetrahedron, 1996, 37, 12177; T. Honda, M. Katoh and S. Yamane, J. Chem. Soc., Perkin Trans. 1, 1996, 2219; T. Honda and M. Katoh, Chem. Commun., 1997, 369.
20. T. Honda, S. Yamane, K. Naito, K. and Y. Suzuki, Heterocycles, 1994, 37, 515; T. Honda, F. Ishikawa and S. Yamane, J. Chem. Soc., Chem. Commun., 1994, 499; T. Honda, S. Yamane, K. Naito and Y. Suzuki, Heterocycles, 1995, 40, 301; T. Honda, F. Ishikawa and S. Yamane, J. Chem. Soc., Perkin Trans. 1, 1996, 1125; T. Honda, S. Yamane, F. Ishikawa and M. Katoh, Tetrahedron, 1996, 37, 12177; T. Honda, M. Katoh and S. Yamane, J. Chem. Soc., Perkin Trans. 1, 1996, 2219; T. Honda and M. Katoh, Chem. Commun., 1997, 369.
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22. The starting phenylalanine derivatives were prepared from the methyl ester by the known procedures; N-methyl derivative: M. C. Allen, W. Fuhrer, B. Tuck, R. Wade and J. M. Wood, J. Med. Chem., 1989, 32, 1652; N,N-dimethyl derivative: T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki and M. Kumada, J. Org. Chem., 1983, 48, 2195; N-benzyl derivative: F. Effenberger, U. Burkard and J. Willfahrt, Liebigs Ann. Chem., 1986, 314; N,N-dibenzyl derivative: B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329; N-acetyl derivative: M. J. Burk, J. E. Feaster, E. H. Harlow and L. Richard, Tetrahedron: Asymmetry, 1991, 2, 569; N-Boc derivative: M. Sakaitani and Y. Ohfune, J. Org. Chem., 1990, 55, 870.
23. The starting phenylalanine derivatives were prepared from the methyl ester by the known procedures; N-methyl derivative: M. C. Allen, W. Fuhrer, B. Tuck, R. Wade and J. M. Wood, J. Med. Chem., 1989, 32, 1652; N,N-dimethyl derivative: T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki and M. Kumada, J. Org. Chem., 1983, 48, 2195; N-benzyl derivative: F. Effenberger, U. Burkard and J. Willfahrt, Liebigs Ann. Chem., 1986, 314; N,N-dibenzyl derivative: B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329; N-acetyl derivative: M. J. Burk, J. E. Feaster, E. H. Harlow and L. Richard, Tetrahedron: Asymmetry, 1991, 2, 569; N-Boc derivative: M. Sakaitani and Y. Ohfune, J. Org. Chem., 1990, 55, 870.
24. The starting phenylalanine derivatives were prepared from the methyl ester by the known procedures; N-methyl derivative: M. C. Allen, W. Fuhrer, B. Tuck, R. Wade and J. M. Wood, J. Med. Chem., 1989, 32, 1652; N,N-dimethyl derivative: T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki and M. Kumada, J. Org. Chem., 1983, 48, 2195; N-benzyl derivative: F. Effenberger, U. Burkard and J. Willfahrt, Liebigs Ann. Chem., 1986, 314; N,N-dibenzyl derivative: B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329; N-acetyl derivative: M. J. Burk, J. E. Feaster, E. H. Harlow and L. Richard, Tetrahedron: Asymmetry, 1991, 2, 569; N-Boc derivative: M. Sakaitani and Y. Ohfune, J. Org. Chem., 1990, 55, 870.
25. The starting phenylalanine derivatives were prepared from the methyl ester by the known procedures; N-methyl derivative: M. C. Allen, W. Fuhrer, B. Tuck, R. Wade and J. M. Wood, J. Med. Chem., 1989, 32, 1652; N,N-dimethyl derivative: T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki and M. Kumada, J. Org. Chem., 1983, 48, 2195; N-benzyl derivative: F. Effenberger, U. Burkard and J. Willfahrt, Liebigs Ann. Chem., 1986, 314; N,N-dibenzyl derivative: B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329; N-acetyl derivative: M. J. Burk, J. E. Feaster, E. H. Harlow and L. Richard, Tetrahedron: Asymmetry, 1991, 2, 569; N-Boc derivative: M. Sakaitani and Y. Ohfune, J. Org. Chem., 1990, 55, 870.
26. The starting phenylalanine derivatives were prepared from the methyl ester by the known procedures; N-methyl derivative: M. C. Allen, W. Fuhrer, B. Tuck, R. Wade and J. M. Wood, J. Med. Chem., 1989, 32, 1652; N,N-dimethyl derivative: T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki and M. Kumada, J. Org. Chem., 1983, 48, 2195; N-benzyl derivative: F. Effenberger, U. Burkard and J. Willfahrt, Liebigs Ann. Chem., 1986, 314; N,N-dibenzyl derivative: B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329; N-acetyl derivative: M. J. Burk, J. E. Feaster, E. H. Harlow and L. Richard, Tetrahedron: Asymmetry, 1991, 2, 569; N-Boc derivative: M. Sakaitani and Y. Ohfune, J. Org. Chem., 1990, 55, 870.
27. The starting phenylalanine derivatives were prepared from the methyl ester by the known procedures; N-methyl derivative: M. C. Allen, W. Fuhrer, B. Tuck, R. Wade and J. M. Wood, J. Med. Chem., 1989, 32, 1652; N,N-dimethyl derivative: T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki and M. Kumada, J. Org. Chem., 1983, 48, 2195; N-benzyl derivative: F. Effenberger, U. Burkard and J. Willfahrt, Liebigs Ann. Chem., 1986, 314; N,N-dibenzyl derivative: B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329; N-acetyl derivative: M. J. Burk, J. E. Feaster, E. H. Harlow and L. Richard, Tetrahedron: Asymmetry, 1991, 2, 569; N-Boc derivative: M. Sakaitani and Y. Ohfune, J. Org. Chem., 1990, 55, 870.
28. N-Benzylproline methyl ester was prepared from methyl prolinate: V. Ferey, P. Vedrenne, L. Toupet, T. L. Gall and C. Mioskowski, J. Org. Chem., 1996, 61, 7244; isopropyl 4-tert-butyldimethylsiloxyprolinate was prepared by silylation of the corresponding ester, which on N-benzylation with BnBr and NaH gave the N-benzyl derivative.
29. 2O.
30. 2O; the N-Boc derivative was prepared according to the known procedure: S. Aoyagi, T.-C. Wang and C. Kibayashi, J. Am. Chem. Soc., 1993, 115, 11393.
31. 2O; the N-Boc derivative was prepared according to the known procedure: S. Aoyagi, T.-C. Wang and C. Kibayashi, J. Am. Chem. Soc., 1993, 115, 11393.
32. J. Inanaga, M. Ishikawa and M. Yamaguchi, Chem. Lett., 1987, 1485.