NAD(P)+-NAD(P)H Models. 87. Nonsteric Stereochemistry Controlled by a Carbonyl Dipole

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 6, 1996, Pages 1679-1685

  Ohno, Atsuyoshi ^a   Tsutsumi, Akihiro ^a   Yamazaki, Norimasa ^a   Okamura, Mutsuo ^b   Mikata, Yuji ^c   Fujii, Masayuki ^d  

^a KYOTO UNIVERSITY   (Japan)

^b NIIGATA UNIVERSITY   (Japan)

^c NARA WOMEN'S UNIVERSITY   (Japan)

^d KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001507149     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1679     Document Type: Article

References (16)

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2. M. Okamura, T. Kashiwagi, Y. Mikata, T. Maruyama, and A. Ohno, Tetrahedron Lett., 32, 1475 (1991).
3. K. P. Nambiar, D. M. Stauffer, P. A. Lolodziej, and S. A. Benner, J. Am. Chem. Soc., 105, 5886 (1983).
4. N. T. Anh and O. Eisenstein, Nouv. J. Chim., 1, 61 (1977).
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6. A. S. Cieplak, J. Am. Chem. Soc., 103, 4540 (1981).
7. M. Okamura, Y. Mikata, N. Yamazaki, A. Tsutsumi, and A. Ohno, Bull. Chem. Soc. Jpn., 66, 1197 (1993).
8. Y. Ohnishi, M. Kagami, and A. Ohno, J. Am. Chem. Soc., 97, 4766 (1975).
9. A. Ohno, A. Tsutsumi, Y. Kawai, N, Yamazaki, Y. Mikata, and M. Okamura, J. Am. Chem. Soc., 116, 8133 (1994).
10. Dihedral angle between the flatt plane of pyridinium moiety and that which includes the carbonyl group are 59.6° and 45.3 based on calculations and experiments, respectively.
11. + elucidated by calculation is 58.1°.
12. Syn- and anti-hydrogens denote those occupying the same face as the carbonyl oxygen and the other face, respectively.
13. A. Ohno, H. Kimura, S. Oka, and Y. Ohnishi, Tetrahedron Lett., 1978, 757.
14. A. Ohno, N. Yamazaki, M. Okamura, Y. Kawai, A. Tsutsumi, and M. Fujii, Bull. Chem. Soc. Jpn., 69, 1093 (1996).
15. Cf. In certain systems, stereochemical result is different in the reactions with these reducing agents: A. Ohno, M. Ogawa, and S. Oka, Tetrahedron Lett., 29, 1951 (1988).
16. A. Ohno, "Proc. 14th Internat. Conf. Biochem.," Prague, Abstr., Vol. 2, p. 217 (1989).