Unexpected influence and its origin in rationally tuning the electronic effect of catalysts in the asymmetric borane reduction of ketones

Journal of Molecular Catalysis A: Chemical

Volumn 284, Issue 1-2, 2008, Pages 40-45

  Du, Juanjuan ^a   Li, Zhiyi ^a   Du, Da Ming ^a   Xu, Jiaxi ^a,b  

^a PEKING UNIVERSITY   (China)

^b BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

Asymmetric reduction; Borane; Electronic effect; Enantioselectivity; Ketone

Indexed keywords

CATALYSTS; DIMERIZATION; ELECTRON TRANSPORT PROPERTIES; ENANTIOSELECTIVITY; HYDRIDES; REDOX REACTIONS;

ASYMMETRIC REDUCTION; BORANE; CATALYST DIMERIZATION; ELECTRONIC EFFECTS;

KETONES;

EID: 40849118159     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2008.01.018     Document Type: Article

References (54)

1. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. (2004), John Wiley, New York
2. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), John Wiley, New York
3. Murahashi S.-I. Ruthenium in Organic Synthesis (2004), John Wiley, New York
4. For examples, see:
5. Wong H.L., Tian Y., and Chan K.S. Tetrahedron Lett. 41 (2000) 7723
6. Corey E.J., Bo Y.X., and Busch-Petersen J. J. Am. Chem. Soc. 120 (1998) 13000
7. Wieger A., and Scharf H.D. Tetrahedron: Asymmetry 7 (1996) 2303
8. Yokomatsu T., Yamagishi T., and Shibuya S. Tetrahedron: Asymmetry 4 (1993) 1783
9. List B., Pojarliev P., Biller W.T., and Martin H.J. J. Am. Chem. Soc. 124 (2002) 827
10. Ma L.G., Jiao P., Zhang Q.H., and Xu J.X. Tetrahedron: Asymmetry 16 (2005) 3718
11. Ma L.G., Jiao P., Zhang Q.H., Du D.M., and Xu J.X. Tetrahedron: Asymmetry 18 (2007) 878
12. For a recent review, see:
13. Flanangan S.P., and Guiry P.J. J. Organomet. Chem. 691 (2006) 2125
14. Jacobsen E.N., Zhang W., and Güler M.L. J. Am. Chem. Soc. 113 (1991) 6703
15. Palucki M., Finney N.S., Pospisil P.J., Güler M.L., Ishida T., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 948
16. Busacca C.A., Grossbach D., So R.C., O'Brien E.M., and Spinelli E.M. Org. Lett. 5 (2003) 595
17. Nakagawa H., Sei Y., Yamaguchi K., Nagano T., and Higuchi T. Tetrahedron: Asymmetry 15 (2004) 3861
18. For recent examples, see:
19. Tu T., Hou X.L., and Dai L.X. J. Organomet. Chem. 689 (2004) 3847
20. Fu Y., Hou G.H., Xie J.H., Xing L., Wang L.X., and Zhou Q.L. J. Org. Chem. 69 (2004) 8157
21. Jeulin S., De Paule S.D., Ratovelomanana-Vidal V., Genet J.P., Champion N., and Dellis P. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5799
22. Cavallo L., and Jacobsen H. J. Org. Chem. 68 (2003) 6202
23. Jew S.S., Yoo M.S., Jeong B.S., Park I.Y., and Park H.G. Org. Lett. 4 (2002) 4245
24. For examples on the influence of the electronic effects of both substrates and ligands on the enantioselectivity, see:
25. Liu H., and Xu J.X. J. Mol. Catal. A: Chem. 244 (2006) 68
26. Tang Z., Jiang F., Cui X., Gong L.Z., Mi A.Q., Jiang Y.Z., and Wu Y.D. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5755
27. Nelson D.W., Gypser A., Ho P.T., Kolb H.C., Kondo T., Kwong H.L., McGrath D.V., Rubin A.E., Norrby P.O., Gable K.P., and Sharpless K.B. J. Am. Chem. Soc. 119 (1997) 1840
28. For recent reviews, see:
29. Jones G.B., and Chapman B.J. Synthesis (1995) 475
30. Jones G.B. Tetrahedron 57 (2001) 7999
31. Castonguay L.A., Rappe A.K., and Casewit C.J. J. Am. Chem. Soc. 113 (1991) 7177
32. Kolb H.C., Andersson P.G., and Sharpless K.B. J. Am. Chem. Soc. 116 (1994) 1278
33. Quan R.W., Li Z., and Jacobsen E.N. J. Am. Chem. Soc. 118 (1996) 8156
34. Brandt P., Roth P., and Andersson P. J. Org. Chem. 69 (2004) 4885
35. For reviews, see:
36. Corey E.J., and Helal C.J. Angew. Chem. Int. Ed. 37 (1998) 1986
37. Cho B.T. Tetrahedron 62 (2006) 7621
38. Deloux L., and Srebnik M. Chem. Rev. 93 (1993) 763
39. Corey E.J., Bakshi R.K., and Shibata S.J. J. Am. Chem. Soc. 109 (1987) 5551
40. Corey E.J., Bakshi R.K., Shibata S., Chen C., and Singh V.K. J. Am. Chem. Soc. 109 (1987) 7925
41. Alagona G., Ghio C., Persico M., and Tomasi S.J. J. Am. Chem. Soc. 125 (2003) 10027
42. Gilmore N.J., and Jones S. Tetrahedron: Asymmetry 14 (2003) 2115
43. Xu J.X., Wei T.Z., Lin S.S., and Zhang Q.H. Helv. Chim. Acta 88 (2005) 180
44. Xu J.X., Wei T.Z., and Zhang Q.H. J. Org. Chem. 68 (2003) 10146 (and cited therein)
45. Wang X., Du J.J., Liu H., Du D.M., and Xu J.X. Heteroat. Chem. 18 (2007) 740 (and cited therein)
46. Corey E.J., and Helal C.J. Tetrahedron Lett. 36 (1995) 9153
47. Xu J.X., Wei T.Z., and Zhang Q.H. J. Org. Chem. 69 (2004) 6860 (and cited therein)
48. Jones T.K., Mohan J.J., Xavier L.C., Blacklock T.J., Mathre D.J., Sohar P., Jones E.T., Reamer R.A., Roberts F.E., and Grabowski E.J. J. Org. Chem. 56 (1991) 763
49. Corey E.J., Link J.O., and Bakshi R.K. Tetrahedron Lett. 33 (1992) 7107
50. Linney L.P., Self C.R., and Williams I.H. J. Chem. Soc. Chem. Commun. (1994) 1651
51. The Hammett constants (σ) cited are all taken from:
52. Hansch C., Leo A., and Taft R.W. Chem. Rev. 91 (1991) 165
53. Xu J.X., Su X.B., and Zhang Q.H. Q. Tetrahedron: Asymmetry 14 (2003) 1781
54. Xu J.X., Lan Y., Wei T.Z., and Zhang Q.H. Chin. J. Chem. 23 (2005) 1457