Asymmetric borane reduction of prochiral ketones catalyzed by C3-symmetric sulfonamide

Tetrahedron Asymmetry

Volumn 19, Issue 7, 2008, Pages 816-821

  Li, Gao Qiang ^a   Yan, Ze Yi ^b   Niu, Yan Ning ^a   Wu, Lu Yong ^a   Wei, Hai Long ^a   Liang, Yong Min ^a  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; KETONE DERIVATIVE; SULFONAMIDE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; ELECTRON TRANSPORT; ENANTIOMER; ENANTIOSELECTIVITY; OPTICAL ROTATION; PRIORITY JOURNAL; REDUCTION;

EID: 43049149004     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.03.012     Document Type: Article

References (37)

1. Moberg C. Angew. Chem., Int. Ed. 37 (1998) 248-268
2. Zhou J., and Tang Y. Chem. Soc. Rev. 34 (2005) 664-676
3. Burk M.J., and Harlow R.L. Angew. Chem. 102 (1990) 1511-1513
4. Angew. Chem., Int. Ed. Engl. 29 (1990) 1462-1464
5. Burk M.J., Feaster J.E., and Harlow R.L. Tetrahedron: Asymmetry 2 (1991) 569-592
6. Chan T.-H., and Zheng G.-Z. Can. J. Chem. 75 (1997) 629-633
7. Kawasaki K., Tsumara S., and Katsuki T. Synlett (1995) 1245-1246
8. Kawasaki K., and Katsuki T. Tetrahedron 53 (1997) 6337-6350
9. Kohmura Y., and Katsuki T. Tetrahedron Lett. 41 (2001) 3941-3945
10. Zhou J., and Tang Y. J. Am. Chem. Soc. 124 (2002) 9030-9031
11. Ye M.-C., Zhou J., Huang Z.-Z., and Tang Y. Chem. Commun. (2003) 2554-2555
12. Zhou J., and Tang Y. Org. Biomol. Chem. 2 (2004) 429-433
13. Fang T., Xu J.-X., and Du D.-M. Synlett (2006) 1559-1563
14. Du D.-M., Fang T., Xu J.-X., and Zhang S.-W. Org. Lett. 8 (2006) 1327-1330
15. Fan Q.-H., Li Y.-M., and Chan A.S.C. Chem. Rev. 102 (2002) 3385-3466
16. Heitbaum M., Glorius F., and Escher L. Angew. Chem., Int. Ed. 45 (2006) 4732-4762
17. Ding K., Wang Z., Wang X., Liang Y., and Wang X. Chem. Eur. J. 12 (2006) 5188-5197
18. Hirao A., Itsuno S., Nakahama N., and Yamazaki N. J. Chem. Soc., Chem. Commun. (1981) 315-317
19. Itsuno S., Ito K., Hirao A., Nakahama S., and Yamazaki N.. J. Chem. Soc., Chem. Commun. (1983) 469-470
20. Itsuno S., and Ito K. J. Org. Chem. 49 (1984) 555-557
21. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551-5553
22. Corey E.J., Bakshi R.K., Shibata S., Chen C.-P., and Singh V.K. J. Am. Chem. Soc. 109 (1987) 7925-7926
23. Deloux L., and Srebnik M. Chem. Rev. 93 (1993) 763-784
24. Wallbaum S., and Martens J. Tetrahedron: Asymmetry 3 (1992) 1475-1504
25. Deninno M.P., Perner R.J., Morton H.E., and DiDomenico S. J. Org. Chem. 57 (1992) 7115-7118
26. Bach J., Berenguer R., Garcia J., Loscertales T., and Vilarrasa J. J. Org. Chem. 61 (1966) 9021-9025
27. Quallich G.J., Blake J.F., and Woodall T.M. J. Am. Chem. Soc. 116 (1994) 8516-8525
28. Jiang B., Feng Y., and Zheng J. Tetrahedron Lett. 41 (2000) 10281-10283
29. Hu J.-B., Zhao G., and Ding Z.-D. Angew. Chem., Int. Ed. 40 (2001) 1109-1111
30. Hu J.-B., Zhao G., Yang G.-S., and Ding Z.-D. J. Org. Chem. 66 (2001) 303-304
31. Zhao G., Hu J.-B., Qian Z.-S., and Yin W.-X. Tetrahedron: Asymmetry 13 (2002) 2095-2098
32. Yang S.-D., Shi Y., Sun Z.-H., Zhao Y.-B., and Liang Y.-M. Tetrahedron: Asymmetry 17 (2006) 1895-1900
33. Xu J., Wei T., and Zhang Q. J. Org. Chem. 68 (2003) 10146-10151
34. Cozzi P.G., and Kotrusz P. J. Am. Chem. Soc. 128 (2006) 4940-4941
35. Liu P.-N., Wang P.-M., and Tu Y.-Q. Org. Lett. 6 (2004) 169-172
36. Cortez N.A., Aguirre P.-H., Parra-Hake M., and Somanathan R. Tetrahedron Lett. 48 (2007) 4335-4338
37. Gamble M.P., Smith A.R.C., and Wills M. J. Org. Chem. 63 (1998) 6068-6071