Stereospecific 4-hydrogen transfer in the asymmetric reduction using (Ss)-3-(p-tolylsulfinyl)-1,4-dihydropyridines, NADH model compounds

Chemistry Letters

Volumn , Issue 10, 1996, Pages 853-854

  Obika, Satoshi ^a   Nishiyama, Toshihiko ^a   Tatematsu, Satoshi ^a   Miyashita, Kazuyuki ^a   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030355156     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.853     Document Type: Article

References (24)

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5. (b) T. Imanishi, S. Obika, T. Nishiyama, M. Nishimoto, Y. Hamano, K. Miyashita, and C. Iwata, Chem. Pharm. Bull, 44, 267 (1996).
6. MOPAC ver.6 coded by J.J.P. Stewart: J.J.P. Stewart, QCPE Bull., 9, 10 (1989). Revised as ver.6.01 by Y. Inoue, for FACOM machine: Y. Inoue, JCPE Newsletter, 3, 49 (1991). Revised as ver.6.02 by T. Takagi's group, for NEC SX-2N machine: T. Takagi , K. Matsumura, A. Noda, N. Onozawa, and H. Fujiwara, Bulletin of Computation Center Osaka University, 22, 1 (1992). Numerical calculations were performed with a SX-2N computer system at the Computation Center, Osaka University.
7. MOPAC ver.6 coded by J.J.P. Stewart: J.J.P. Stewart, QCPE Bull., 9, 10 (1989). Revised as ver.6.01 by Y. Inoue, for FACOM machine: Y. Inoue, JCPE Newsletter, 3, 49 (1991). Revised as ver.6.02 by T. Takagi's group, for NEC SX-2N machine: T. Takagi , K. Matsumura, A. Noda, N. Onozawa, and H. Fujiwara, Bulletin of Computation Center Osaka University, 22, 1 (1992). Numerical calculations were performed with a SX-2N computer system at the Computation Center, Osaka University.
8. MOPAC ver.6 coded by J.J.P. Stewart: J.J.P. Stewart, QCPE Bull., 9, 10 (1989). Revised as ver.6.01 by Y. Inoue, for FACOM machine: Y. Inoue, JCPE Newsletter, 3, 49 (1991). Revised as ver.6.02 by T. Takagi's group, for NEC SX-2N machine: T. Takagi , K. Matsumura, A. Noda, N. Onozawa, and H. Fujiwara, Bulletin of Computation Center Osaka University, 22, 1 (1992). Numerical calculations were performed with a SX-2N computer system at the Computation Center, Osaka University.
9. S.D. Kahn and W.J. Hehre, J. Am. Chem. Soc., 108, 7399 (1986); R.W. Hoffmann, Chem. Rev., 89, 1841 (1989) and references cited therein.
10. S.D. Kahn and W.J. Hehre, J. Am. Chem. Soc., 108, 7399 (1986); R.W. Hoffmann, Chem. Rev., 89, 1841 (1989) and references cited therein.
11. 6 were 3.36 and 2.58 ppm, while those of 2 were 3.58 and 2.57 ppm, respectively.
12. 3a
13. Synthesis of the 4-monodeuterated model having a chiral auxirialy was reported by S.G. Davies' group: S.G. Davies, A.J. Edwards, R.T. Skerlj, K.H. Sutton, and M. Whittaker, J. Chem. Soc., Perkin Trans. 1, 1991, 1027. For recent examples: A. Ohno, A. Tsutsumi, Y. Kawai, N. Yamazaki, Y. Mikata, and M. Okamura, J. Am. Chem. Soc., 116, 8133 (1994); A. Ohno, N. Yamazaki, M. Okamura, Y. Kawai, A. Tsutsumi, Y. Mikata, and M. Fujii, Bull. Chem. Soc. Jpn., 69, 1093 (1996).
14. Synthesis of the 4-monodeuterated model having a chiral auxirialy was reported by S.G. Davies' group: S.G. Davies, A.J. Edwards, R.T. Skerlj, K.H. Sutton, and M. Whittaker, J. Chem. Soc., Perkin Trans. 1, 1991, 1027. For recent examples: A. Ohno, A. Tsutsumi, Y. Kawai, N. Yamazaki, Y. Mikata, and M. Okamura, J. Am. Chem. Soc., 116, 8133 (1994); A. Ohno, N. Yamazaki, M. Okamura, Y. Kawai, A. Tsutsumi, Y. Mikata, and M. Fujii, Bull. Chem. Soc. Jpn., 69, 1093 (1996).
15. Synthesis of the 4-monodeuterated model having a chiral auxirialy was reported by S.G. Davies' group: S.G. Davies, A.J. Edwards, R.T. Skerlj, K.H. Sutton, and M. Whittaker, J. Chem. Soc., Perkin Trans. 1, 1991, 1027. For recent examples: A. Ohno, A. Tsutsumi, Y. Kawai, N. Yamazaki, Y. Mikata, and M. Okamura, J. Am. Chem. Soc., 116, 8133 (1994); A. Ohno, N. Yamazaki, M. Okamura, Y. Kawai, A. Tsutsumi, Y. Mikata, and M. Fujii, Bull. Chem. Soc. Jpn., 69, 1093 (1996).
16. -1).
17. P. van Erikeren, P. Kenney, and R. Tokmakian, J. Am. Chem. Soc., 101, 7402 (1979); S. Yasui, K. Nakamura, A. Ohno, and S. Oka, Bull. Chem. Soc. Jpn., 55, 196 (1982); A. Ohno, T. Shio, H. Yamamoto, and S. Oka, J. Am. Chem. Soc. 103, 2045 (1981); S. Shinkai, T. Tsuno, Y. Asatani, and O. Manabe, J. Chem. Soc., Perkin Trans. 2, 1983, 1533; B.W. Carlson, L.L. Miller, P. Neta, and J. Grodkowski, J. Am. Chem. Soc., 106, 7233 (1984); S. Fukuzumi, N. Nishizawa, and T. Tanaka, J. Org. Chem., 49, 3571 (1984).
18. P. van Erikeren, P. Kenney, and R. Tokmakian, J. Am. Chem. Soc., 101, 7402 (1979); S. Yasui, K. Nakamura, A. Ohno, and S. Oka, Bull. Chem. Soc. Jpn., 55, 196 (1982); A. Ohno, T. Shio, H. Yamamoto, and S. Oka, J. Am. Chem. Soc. 103, 2045 (1981); S. Shinkai, T. Tsuno, Y. Asatani, and O. Manabe, J. Chem. Soc., Perkin Trans. 2, 1983, 1533; B.W. Carlson, L.L. Miller, P. Neta, and J. Grodkowski, J. Am. Chem. Soc., 106, 7233 (1984); S. Fukuzumi, N. Nishizawa, and T. Tanaka, J. Org. Chem., 49, 3571 (1984).
19. P. van Erikeren, P. Kenney, and R. Tokmakian, J. Am. Chem. Soc., 101, 7402 (1979); S. Yasui, K. Nakamura, A. Ohno, and S. Oka, Bull. Chem. Soc. Jpn., 55, 196 (1982); A. Ohno, T. Shio, H. Yamamoto, and S. Oka, J. Am. Chem. Soc. 103, 2045 (1981); S. Shinkai, T. Tsuno, Y. Asatani, and O. Manabe, J. Chem. Soc., Perkin Trans. 2, 1983, 1533; B.W. Carlson, L.L. Miller, P. Neta, and J. Grodkowski, J. Am. Chem. Soc., 106, 7233 (1984); S. Fukuzumi, N. Nishizawa, and T. Tanaka, J. Org. Chem., 49, 3571 (1984).
20. P. van Erikeren, P. Kenney, and R. Tokmakian, J. Am. Chem. Soc., 101, 7402 (1979); S. Yasui, K. Nakamura, A. Ohno, and S. Oka, Bull. Chem. Soc. Jpn., 55, 196 (1982); A. Ohno, T. Shio, H. Yamamoto, and S. Oka, J. Am. Chem. Soc. 103, 2045 (1981); S. Shinkai, T. Tsuno, Y. Asatani, and O. Manabe, J. Chem. Soc., Perkin Trans. 2, 1983, 1533; B.W. Carlson, L.L. Miller, P. Neta, and J. Grodkowski, J. Am. Chem. Soc., 106, 7233 (1984); S. Fukuzumi, N. Nishizawa, and T. Tanaka, J. Org. Chem., 49, 3571 (1984).
21. P. van Erikeren, P. Kenney, and R. Tokmakian, J. Am. Chem. Soc., 101, 7402 (1979); S. Yasui, K. Nakamura, A. Ohno, and S. Oka, Bull. Chem. Soc. Jpn., 55, 196 (1982); A. Ohno, T. Shio, H. Yamamoto, and S. Oka, J. Am. Chem. Soc. 103, 2045 (1981); S. Shinkai, T. Tsuno, Y. Asatani, and O. Manabe, J. Chem. Soc., Perkin Trans. 2, 1983, 1533; B.W. Carlson, L.L. Miller, P. Neta, and J. Grodkowski, J. Am. Chem. Soc., 106, 7233 (1984); S. Fukuzumi, N. Nishizawa, and T. Tanaka, J. Org. Chem., 49, 3571 (1984).
22. P. van Erikeren, P. Kenney, and R. Tokmakian, J. Am. Chem. Soc., 101, 7402 (1979); S. Yasui, K. Nakamura, A. Ohno, and S. Oka, Bull. Chem. Soc. Jpn., 55, 196 (1982); A. Ohno, T. Shio, H. Yamamoto, and S. Oka, J. Am. Chem. Soc. 103, 2045 (1981); S. Shinkai, T. Tsuno, Y. Asatani, and O. Manabe, J. Chem. Soc., Perkin Trans. 2, 1983, 1533; B.W. Carlson, L.L. Miller, P. Neta, and J. Grodkowski, J. Am. Chem. Soc., 106, 7233 (1984); S. Fukuzumi, N. Nishizawa, and T. Tanaka, J. Org. Chem., 49, 3571 (1984).
23. In the reduction with NADH, the 4-hydrogen which is syn with respect to the amide carbonyl group is known to be stereospecifically transformed: Y.-D. Wu and K.N. Houk, J. Am. Chem. Soc., 113, 2353 (1991). For recent example: J. Bédat, V. Levacher, G. Dupas, G. Quéguiner, and J. Bourguignon, Chem. Lett., 1996, 359.
24. In the reduction with NADH, the 4-hydrogen which is syn with respect to the amide carbonyl group is known to be stereospecifically transformed: Y.-D. Wu and K.N. Houk, J. Am. Chem. Soc., 113, 2353 (1991). For recent example: J. Bédat, V. Levacher, G. Dupas, G. Quéguiner, and J. Bourguignon, Chem. Lett., 1996, 359.