Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline

Tetrahedron Asymmetry

Volumn 16, Issue 6, 2005, Pages 1157-1165

  Terakado, Dai ^a   Koutaka, Hitomi ^a   Oriyama, Takeshi ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; DIAMINE DERIVATIVE; PROLINE;

ACYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHIRALITY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 14944370701     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.01.034     Document Type: Article

References (47)

1. F. Theil Chem. Rev. 95 1995 2203 2227
2. C.-S. Chen, and C. Sih Angew. Chem., Int. Ed. Engl. 28 1989 695 707
3. A.M. Klibanov Acc. Chem. Res. 23 1990 114 120
4. Z.-F. Xie Tetrahedron: Asymmetry 2 1991 733 750
5. E. Vedejs, and O. Daugulis J. Am. Chem. Soc. 121 1999 5813 5814
6. E. Vedejs, and J.A. MacKay Org. Lett. 3 2001 535 536
7. E. Vedejs, O. Daugulis, J.A. MacKay, and E. Rozners Synlett 2001 1499 1505
8. E. Vedejs, and O. Daugulis J. Am. Chem. Soc. 125 2003 4166 4173
9. J.A. MacKay, and E. Vedejs J. Org. Chem. 69 2004 6934 6937
10. J.C. Ruble, H.A. Latham, and G.C. Fu J. Am. Chem. Soc. 119 1997 1492 1493
11. C.E. Garrett, and G.C. Fu J. Am. Chem. Soc. 120 1998 7479 7483
12. B. Tao, J.C. Ruble, D.A. Hoic, and G.C. Fu J. Am. Chem. Soc. 121 1999 5091 5092
13. J.C. Ruble, J. Tweddell, and G.C. Fu J. Org. Chem. 63 1998 2794 2795
14. S. Bellemin-Laponnaz, J. Tweddell, J.C. Ruble, F.M. Breitling, and G.C. Fu Chem. Commun. 2000 1009 1010
15. G.C. Fu Acc. Chem. Res. 33 2000 412 420
16. G.C. Fu Acc. Chem. Res. 37 2004 542 547
17. S.J. Miller, G.T. Copeland, N. Papaioannou, T.E. Horstmann, and E.M. Ruel J. Am. Chem. Soc. 120 1998 1629 1630
18. G.T. Copeland, E.R. Jarvo, and S.J. Miller J. Org. Chem. 63 1998 6784 6785
19. E.R. Jarvo, G.T. Copeland, N. Papaioannou, P.J. Bonitatebus Jr., and S.J. Miller J. Am. Chem. Soc. 121 1999 11638 11643
20. E.R. Jarvo, M.M. Vasbinder, and S.J. Miller Tetrahedron 56 2000 9773 9779
21. E.R. Jarvo, C.A. Evans, G.T. Copeland, and S.J. Miller J. Org. Chem. 66 2001 5522 5527
22. A.C. Spivey, T. Fekner, and S.E. Spey J. Org. Chem. 65 2000 3154 3159
23. A.C. Spivey, A. Maddaford, T. Fekner, A.J. Redgrave, and C.S. Frampton J. Chem. Soc., Perkin Trans. 1 2000 3460 3468
24. A.C. Spivey, A. Maddaford, D.P. Leese, and A.J. Redgrave J. Chem. Soc., Perkin Trans. 1 2001 1785 1794
25. A.C. Spivey, F. Zhu, M.B. Mitchell, S.G. Davey, and R.L. Jarvest J. Org. Chem. 68 2003 7379 7385
26. A.C. Spivey, D.P. Leese, F. Zhu, S.G. Davey, and R.L. Jarvest Tetrahedron 60 2004 4513 4525
27. T. Kawabata, M. Nagato, K. Takasu, and K. Fuji J. Am. Chem. Soc. 119 1997 3169 3170
28. T. Kawabata, K. Yamamoto, Y. Momose, H. Yoshida, Y. Nagaoka, and K. Fuji Chem. Commun. 2001 2700 2701
29. T. Kawabata, R. Stragies, T. Fukaya, Y. Nagaoka, H. Schedel, and K. Fuji Tetrahedron Lett. 44 2003 1545 1548
30. J. Naraku, N. Shimomoto, T. Hanamoto, and J. Inanaga Enantiomer 5 2000 135 138
31. Y. Matsumura, T. Maki, S. Murakami, and O. Onomura J. Am. Chem. Soc. 125 2003 2052 2053
32. T. Oriyama, K. Imai, T. Hosoya, and T. Sano Tetrahedron Lett. 39 1998 397 400
33. T. Oriyama, K. Imai, T. Sano, and T. Hosoya Tetrahedron Lett. 39 1998 3529 3532
34. T. Oriyama, T. Hosoya, and T. Sano Heterocycles 52 2000 1065 1069
35. T. Oriyama, H. Taguchi, D. Terakado, and T. Sano Chem. Lett. 31 2002 26 27
36. T. Oriyama, Y. Hori, K. Imai, and R. Sasaki Tetrahedron Lett. 37 1996 8543 8546
37. T. Sano, K. Imai, K. Ohashi, and T. Oriyama Chem. Lett. 28 1999 265 266
38. T. Sano, H. Miyata, and T. Oriyama Enantiomer 5 2000 119 123
39. T. Sakai, T. Kishimoto, Y. Tanaka, T. Ema, and M. Utaka Tetrahedron Lett. 39 1998 7881 7884
40. J. Ichikawa, M. Asami, and T. Mukaiyama Chem. Lett. 13 1984 949 952
41. V. Partali, A.G. Melbye, T. Alvik, and T. Anthonsen Tetrahedron: Asymmetry 1 1992 65 72
42. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 Wiley New York pp 201-230
43. M. Jungen, and H.-J. Gais Tetrahedron: Asymmetry 10 1999 3747 3758
44. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765 5780
45. S.C. Bergmeier, and P.P. Seth J. Org. Chem. 62 1997 2671 2674
46. A.B. Charette, and H. Lebel Org. Synth., Coll. X 2004 613
47. C.-S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299