Asymmetric reduction of ketoxime O-alkyl ethers with chirally modified NaBH4-ZrCl4

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 7, 1990, Pages 1859-1863

  Itsuno, Shinichi ^a   Sakurai, Yoshiki ^a   Shimizu, Koji ^a   Ito, Koichi ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049089229     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19900001859     Document Type: Article

References (36)

1. M. P. Menachery, G. L. Lavanier, M. L. Wetherly, H. Guinaudeau, and M. Shamma, J. Nat. Prod., 1986, 49, 745.
2. G. Bringmann, in ‘The Alkaloids,' ed. A. Brossi, Academic Press, New York, 1986, vol. 29, p. 141.
3. S. T. Lu, T. L. Su, T. Kametani, A. Ujie, M. Ihara, and K. Fukumoto, Heterocycles, 1975, 3, 459.
4. S. T. Lu and E. C. Wang, Phytochemistry, 1982, 21, 809.
5. S. J. Danishefsky, P. J. Harrison, R. R. Webb, and B. T. O’Neill, J. Am. Chem. Soc., 1985, 107, 1421.
6. A. I. Meyers, D. B. Miller, and F. H. White, J. Am. Chem. Soc., 1988, 110, 4778.
7. A. I. Meyers, Aldrichimica Acta, 1985, 18, 59.
8. R. E. Gawley, K. Rein, and S. Chemburkar, J. Org. Chem., 1989, 54, 3002.
9. H. Takahashi, Y. Suzuki, and H. Inagaki, Chem. Pharm. Bull., 1982, 30, 3160.
10. S. E. Denmark, T. Weber, and D. W. Piotrowski, J. Am. Chem. Soc., 1987, 109, 2224.
11. H. C. Brown, K. Kim, T. E. Cole, and B. Singaram, J. Am. Chem. Soc., 1986, 108, 6761.
12. M. M. Midland, ‘Asymmetric Synthesis,' ed. J. D. Morrison, Academic Press, New York, 1983, vol. 2, p. 45.
13. H. Haubenstock, Top. Stereochem., 1983, 14, 231.
14. S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, and S. Nakahama, Bull. Chem. Soc. Jpn., 1987, 60, 395.
15. S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, and S. Nakahama, J. Chem. Soc., Perkin Trans. 1, 1985, 2039.
16. S. R. Landor, O. O. Sonola, and A. R. Tatchell, J. Chem. Soc., Perkin Trans. 1, 1974, 1902.
17. S. R. Landor, Y. M. Chan, O. O. Sonola, and A. R. Tatchell, J. Chem. Soc., Perkin Trans. 1, 1984, 493.
18. H. Brunner, R. Becker, and S. Gauder, Organometallics, 1986, 4, 739.
19. J. F. Archer, D. R. Boyd, W. R. Jackson, M. F. Grundon, and W. A. Khan, J. Chem. Soc. C, 1971, 2560.
20. S. R. Landor, O. O. Sonola, and A. R. Tatchell, J. Chem. Soc., Perkin Trans. 1, 1987, 605.
21. Bull. Chem. Soc. Jpn., 1984, 57, 1658.
22. A. I. Meyers and J. D. Brown, Tetrahedron Lett., 1988, 29, 5617.
23. S. Itsuno, Y. Sakurai, and K. Ito, Synthesis, 1988, 995.
24. S. Itsuno, Y. Sakurai, K. Shimizu, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1989, 1548.
25. D. W. Chasar, J. Org. Chem., 1971, 36, 613.
26. S. Kano, Y. Tanimoto, E. Sugino, and S. Hibino, Synthesis, 1980, 695.
27. C. Kashima and Y. Yamamoto, Chem. Lett., 1987, 1285.
28. S. W. Heizman and B. Ganem, J. Am. Chem. Soc., 1982, 104, 6801.
29. A. Hirao, M. Ohwa, S. Itsuno, H. Mochizuki, S. Nakahama, and N. Yamazaki, Bull. Chem. Soc. Jpn., 1981, 54, 1424.
30. A. Hirao, S. Nakahama, H. Mochizuki, S. Itsuno, M. Ohwa, and N. Yamazaki, J. Chem. Soc., Chem. Commun., 1979, 807.
31. P. Hodge, ‘Syntheses and Separations Using Functional Polymers,' eds. D. C. Sherrington and P. Hodge, Wiley, Chichester, 1988, p. 43.
32. J. M. J. Fréchet, G. D. Darling, S. Itsuno, P. Z. Lu, M. V. Meftahi, and W. Rolls, Jr., Pure Appi. Chem., 1988, 60, 353.
33. A. C. Cope, C. R. Ganellin, H. W. Johnson, Jr., T. V. Van Auken, and H. J. J. Winkler, J. Am. Chem. Soc., 1963, 85, 3276.
34. C. J. Karabatsos and N. Hsi, Tetrahedron, 1967, 23, 1079.
35. S. Itsuno, A. Hirao, S. Nakahama, and N. Yamazaki, J. Chem. Soc., Perkin Trans. 1, 1983, 1673.
36. S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, and S. Nakahama, Polymer, 1987, 28, 1005.