Catalytic asymmetric borane reduction of prochiral ketones using chiral camphor-derived mercapto-alcohols

Chinese Journal of Chemistry

Volumn 16, Issue 3, 1998, Pages 284-288

  Zhou, Yong Gui ^a   Hou, Xue Long ^a   Dai, Li Xin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric borane reduction; Ketone; Mercapto alcohol

Indexed keywords

EID: 0000076491     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.19980160314     Document Type: Article

References (26)

1. Singh, V. K., Synthesis, 605(1992).
2. a) Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N., J. Chem. Soc., Chem. Commun., 315(1981).
3. b) Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K.; Hirao, A.; Nakahama, S., J. Chem. Soc., Perkin Trans. I, 2039(1985).
4. a) Corey, E.J.; Bakishi, R.K.; Shibata, S., J. Am. Chem. Soc., 109, 5551(1987).
5. b) Corey, E.J.; Azimioara, M.; Sarshar, S., Tetrahedron Lett., 33, 3429(1992).
6. a) Quallich, G.J.; Woodall, J.M., Tetrahedron Lett., 34, 785(1993).
7. b) Bringman, G.; Hartung, T., Angew. Chem., Int. Ed. Engl., 31, 761(1992).
8. c) Rao, A.V.R.; Gurjar, M.K.; Kaiwar, V., Tetrahedron: Asymmetry, 3, 895(1992).
9. d) Tanaka, K.; Matsui, J.; Suzuki, H., J. Chem. Soc., Chem. Commun., 1311(1991).
10. e) Li, X.; Xie, R., Tetrahedron: Asymmetry, 8, 2283(1997).
11. f) Shen, Z.-X.; Lu, J.; Zhang, Q.; Zhang, Y.-W., Tetrahedron: Asymmetry, 8, 2287(1997) and references cited therein.
12. Li, A.-H.; Dai, L-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W., J. Org. Chem., 61, 489(1996).
13. Li, A.-H.; Zhou, Y.-G.; Dai, L-X.; Hou, X.-L.; Xia, L.-J.; Lin, L., Angew. Chem., Int. Ed. Engl., 36, 1317(1997).
14. a) Zhang, J.; Lou, B.; Guo, G.; Dai, L., J. Org. Chem., 56, 1670(1991).
15. b) Hou, X.-L.; Hong, D.-G.; Rong, G.-B.; Guo, Y.-L.; Dai, L.-X., Tetrahedron Lett., 34, 8513(1993).
16. c) Zhang, J.; Lou, B.; Guo, G., Dai, L., Acta Chim. Sin., 50, 913(1992).
17. Jiang, Y.Z.; Feng, X.M.; Gong, L.Z.; Li, Z.; Yang, G.S.; Mi, A.Q., Chin. Chem. Lett., 7, 415(1996).
18. Yang, T.K., The First National Symposium of Organic Chemistry, Oct. 6-10, Chengdu, China, 1997.
19. For 2 see: Lee, D.-H.; Mung, S.-M.; Lai, M.-C.; Chu, T.-Y.; Yang, T.-K., Org. Prep. Procedure Int., 25, 673(1993); for 3 see: Eliel, E.; Fraze, J.W., J. Org. Chem., 44, 3598(1979).
20. For 2 see: Lee, D.-H.; Mung, S.-M.; Lai, M.-C.; Chu, T.-Y.; Yang, T.-K., Org. Prep. Procedure Int., 25, 673(1993); for 3 see: Eliel, E.; Fraze, J.W., J. Org. Chem., 44, 3598(1979).
21. The same effect was also observed by other groups. See also 2b, 3a. a) Jiang, Y.; Qin, Y,; Mi, A.; Huang, Z., Tetrahedron: Asymmetry, 5, 1211(1994).
22. The same effect was also observed by other groups. See also 2b, 3a. a) Jiang, Y.; Qin, Y,; Mi, A.; Huang, Z., Tetrahedron: Asymmetry, 5, 1211(1994). b) Michael, B.J.; Maffei, M.; Buono, G., Tetrahedron: Asymmetry, 4, 2255(1993).
23. The same effect was also observed by other groups. See also 2b, 3a. a) Jiang, Y.; Qin, Y,; Mi, A.; Huang, Z., Tetrahedron: Asymmetry, 5, 1211(1994). b) Michael, B.J.; Maffei, M.; Buono, G., Tetrahedron: Asymmetry, 4, 2255(1993). c) Martens, J.; Dauelsberg, C.; Behnen, W.; Wallbaum, S., Tetrahedron: Asymmetry, 3, 347(1992) and references cited therein.
24. See also 3a, a) Jones, D.K.; Liotta, D.C.; Shinkai, I.; Mathre, D.J., J. Org. Chem., 58, 799(1993). b) Quallich, G.J.; Blake, J.F.; Woodall, T.M., J. Am. Chem. Soc., 116, 8516(1994). c) Corey, E.J.; Link, J. O., Tetrahedron Lett., 30, 6275(1989).
25. See also 3a, a) Jones, D.K.; Liotta, D.C.; Shinkai, I.; Mathre, D.J., J. Org. Chem., 58, 799(1993). b) Quallich, G.J.; Blake, J.F.; Woodall, T.M., J. Am. Chem. Soc., 116, 8516(1994). c) Corey, E.J.; Link, J. O., Tetrahedron Lett., 30, 6275(1989).
26. See also 3a, a) Jones, D.K.; Liotta, D.C.; Shinkai, I.; Mathre, D.J., J. Org. Chem., 58, 799(1993). b) Quallich, G.J.; Blake, J.F.; Woodall, T.M., J. Am. Chem. Soc., 116, 8516(1994). c) Corey, E.J.; Link, J. O., Tetrahedron Lett., 30, 6275(1989).