Asymmetric reduction of prochiral ketones with borane using chiral squaric amino alcohols derived from camphor as catalysts

Journal of Molecular Catalysis A: Chemical

Volumn 242, Issue 1-2, 2005, Pages 57-61

  Zou, Hai Hua ^a   Hu, Jian ^b   Zhang, Ji ^a   You, Jing Song ^a   Ma, Dan ^a   Lü, Ding ^b   Xie, Ru Gang ^a  

^a SICHUAN UNIVERSITY   (China)

^b Hengdian Group Chengdu Molecule Lab Co Ltd   (China)

Author keywords

Asymmetric reduction; Borane; Camphor; Ketone; Squaric acid

Indexed keywords

ALCOHOLS; AMINO ACIDS; CATALYSTS; SYNTHESIS (CHEMICAL);

ASYMMETRIC REDUCTION; BORANE; CAMPHOR; SQUARIC ACID;

KETONES;

EID: 27744493858     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.07.020     Document Type: Article

References (32)

1. S. Wallbaum, and J. Martens Tetrahedron: Asymmetry 3 1992 1475
2. E.J. Corey, and C.J. Helal Angew. Chem. Int. Ed. Engl. 37 1998 1986
3. J. Zhang, H.B. Zhou, and R.G. Xie Curr. Org. Chem. 6 2002 865
4. X.S. Li, and R.G. Xie Tetrahedron: Asymmetry 7 1996 2779
5. X.S. Li, and R.G. Xie Tetrahedron: Asymmetry 8 1997 2283
6. A. Hirao, S. Itsuno, S. Nakahama, and N. Yamazaki J. Chem. Soc. Chem. Commun. 1981 315
7. A. Hirao, S. Itsuno, S. Nakahama, and K. Ito J. Chem. Soc. Chem. Commun. 1983 469
8. E.J. Corey, R.K. Bakshi, and S. Shibata J. Am. Chem. Soc. 109 1987 5551
9. E.J. Corey, R.K. Bakshi, S. Shibata, C.-P. Chen, and V.K. Singh J. Am. Chem. Soc. 109 1987 7925
10. S. Nakanishi, K. Kondo, and K. Takemoto Chem. Express. 2 1987 41
11. K. Tanaka, M. Matsui, and H. Suzuki J. Chem. Soc. Chem. Commun. 1991 1311
12. J.G. Quallich, J.F. Blake, and T.M. Woodall J. Am. Chem. Soc. 116 1994 8516
13. J.C. Fiaud, F. Mazé, and H.B. Kagan Tetrahedron: Asymmetry 9 1998 3647
14. T.K. Yang, and D.S. Lee Tetrahedron: Asymmetry 10 1999 405
15. X.S. Li, C.H. Yeung, A.S.C. Chan, and T.K. Yang Tetrahedron: Asymmetry 10 1999 759
16. V. Santhi, and J.M. Rao Tetrahedron: Asymmetry 11 2000 3553
17. V. Santhi, and J.M. Rao Synth. Commun. 30 2000 4329
18. R. West Oxocarbons 1980 Academic New York
19. A.H. Schmidt Synthesis 1980 961
20. R. Prohens, S. Tomàs, J. Morey, P.M. Deyà, P. Ballester, and A. Costa Tetrahedron Lett. 39 1998 1063
21. D.Q. Yuan, Y.Z. Chen, J.C. Li, and H.m. Zhao Chin. J. Org. Chem. 12 1992 312
22. S. Ferrer, M. Pastó, B. Rodríguez, A. Riera, and M.A. Pericàs Tetrahedron: Asymmetry 14 2003 1747
23. J. Zhang, H.B. Zhou, S.M. Lu, M.M. Luo, R.G. Xie, M.C.K. Choi, Z.Y. Zhou, A.S.C. Chan, and T.K. Yang Tetrahedron: Asymmetry 12 2001 1907
24. H.B. Zhou, J. Zhang, S.M. Lu, R.G. Xie, Z.Y. Zhou, M.C.K. Choi, A.S.C. Chan, and T.K. Yang Tetrahedron 57 2001 9325
25. H.B. Zhou, S.M. Lu, R.G. Xie, A.S.C. Chan, and T.K. Yang Tetrahedron Lett. 42 2001 1107
26. J. Zhang, L.L. Li, H.H. Zou, J.J. Chen, K.B. Yu, and R.G. Xie Chin. J. Chem. 22 2004 585
27. S.M. Lü, H.B. Zhou, J. Zhang, R.G. Xie, Z.Y. Zhou, A.C.S. Chan, and T.K. Yang Chem. J. Chin. Univ. 22 2001 1498
28. J.D. White, D.J. Wardrop, K.F. Sundermann, Org. Syn. 79, 125.
29. R.A. Chittenden, and G.H. Cooper J. Chem. Soc. (C) 1970 49
30. K. Tanaka, H. Ushio, Y. Kawabata, and H. Suzuki J. Chem. Soc., Perkin. Trans. 1 1991 1445
31. H. B. Zhou, Ph. D. Thesis, Sichuan University, 2000.
32. J. Zhang, Ph. D. Thesis, Sichuan University, 2002.