Exploring structural effects of ketone catalysts on asymmetric epoxidation of olefins

Tetrahedron

Volumn 61, Issue 26, 2005, Pages 6409-6417

  Crane, Zackary ^a   Goeddel, David ^a   Gan, Yonghong ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Asymmetric epoxidation; Chiral dioxirane; Chiral ketone; Organocatalysis

Indexed keywords

ALKENE DERIVATIVE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; KETONE; LACTONE; NITROGEN; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; EPOXIDATION; HYDROPHOBICITY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 20444441134     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.123     Document Type: Article

References (55)

1. For general leading references on dioxiranes see: (a) W. Adam, R. Curci, and J.O. Edwards Acc. Chem. Res. 22 1989 205
2. R.W. Murray Chem. Rev. 89 1989 1187
3. R. Curci, A. Dinoi, and M.F. Rubino Pure Appl. Chem. 67 1995 811
4. E.L. Clennan Trends Org. Chem. 5 1995 231
5. W. Adam, C.R. Saha-Möller, and C.-G. Zhao Org. React. 61 2002 219
6. For reviews on chiral ketone catalyzed asymmetric epoxidations see: (a) S.E. Denmark, and Z. Wu Synlett 1999 847
7. M. Frohn, and Y. Shi Synthesis 2000 1979
8. Y. Shi Acc. Chem. Res. 37 2004 488
9. D. Yang Acc. Chem. Res. 37 2004 497
10. For selected examples of asymmetric epoxidation mediated in situ by chiral ketones see: (a) R. Curci, M. Fiorentino, and M.R. Serio J. Chem. Soc., Chem. Commun. 1984 155
11. R. Curci, L. D'Accolti, M. Fiorentino, and A. Rosa Tetrahedron Lett. 36 1995 5831
12. D. Yang, Y.C. Yip, M.W. Tang, M.K. Wong, J.H. Zheng, and K.K. Cheung J. Am. Chem. Soc. 118 1996 491
13. D. Yang, X.-C. Wang, M.-K. Wong, Y.-C. Yip, and M.-W. Tang J. Am. Chem. Soc. 118 1996 11311
14. C.E. Song, Y.H. Kim, K.C. Lee, S.G. Lee, and B.W. Jin Tetrahedron: Asymmetry 8 1997 2921
15. W. Adam, and C.-G. Zhao Tetrahedron: Asymmetry 8 1997 3995
16. S.E. Denmark, Z. Wu, C.M. Crudden, and H. Matsuhashi J. Org. Chem. 62 1997 8288
17. A. Armstrong, and B.R. Hayter Chem. Commun. 1998 621
18. D. Yang, M.-K. Wong, Y.-C. Yip, X.-C. Wang, M.-W. Tang, J.-H. Zheng, and K.-K. Cheung J. Am. Chem. Soc. 120 1998 5943
19. D. Yang, Y.-C. Yip, J. Chen, and K.-K. Cheung J. Am. Chem. Soc. 120 1998 7659
20. W. Adam, C.R. Saha-Möller, and C.-G. Zhao Tetrahedron: Asymmetry 10 1999 2749
21. A. Solladie-Cavallo, and L. Bouerat Org. Lett. 2 2000 3531
22. A. Solladie-Cavallo, L. Bouerat, and L. Jierry J. Org. Chem. 2001 4557
23. O. Bortolini, M. Fogagnolo, G. Fantin, S. Maietti, and A. Medici Tetrahedron: Asymmetry 12 2001 1113
24. M. Seki, T. Furutani, R. Imashiro, T. Kuroda, T. Yamanaka, N. Harada, H. Arakawa, M. Kusama, and T. Hashiyama Tetrahedron Lett. 42 2001 8201
25. K. Matsumoto, and K. Tomioka Tetrahedron Lett. 43 2002 631
26. T.K.M. Shing, and G.Y.C. Leung Tetrahedron 58 2002 7545
27. O. Bortolini, G. Fantin, M. Fogagnolo, R. Forlani, S. Maietti, and P. Pedrini J. Org. Chem. 67 2002 5802
28. C.J. Stearman, and V. Behar Tetrahedron Lett. 43 2002 1943
29. S.E. Denmark, and H. Matsuhashi J. Org. Chem. 67 2002 3479
30. A. Armstrong, G. Ahmed, B. Dominguez-Fernandez, B.R. Hayter, and J.S. Wailes J. Org. Chem. 67 2002 8610
31. W.-K. Chan, W.-Y. Yu, C.-M. Che, and M.-K. Wong J. Org. Chem. 68 2003 6576
32. G. Bez, and C.-G. Zhao Tetrahedron Lett. 44 2003 7403
33. For examples of asymmetric epoxidation mediated by fructose-derived ketone 1 see (a) Y. Tu, Z.-X. Wang, and Y. Shi J. Am. Chem. Soc. 118 1996 9806
34. Z.-X. Wang, Y. Tu, M. Frohn, J.-R. Zhang, and Y. Shi J. Am. Chem. Soc. 119 1997 11224
35. L. Shu, and Y. Shi Tetrahedron 57 2001 5213
36. Y. Tu, M. Frohn, Z.-X. Wang, and Y. Shi Org. Synth. 80 2003 1
37. Z.-X. Wang, L. Shu, M. Frohn, Y. Tu, and Y. Shi Org. Synth. 80 2003 9
38. H. Tian, X. She, L. Shu, H. Yu, and Y. Shi J. Am. Chem. Soc. 122 2000 11551
39. H. Tian, X. She, J. Xu, and Y. Shi Org. Lett. 3 2001 1929
40. H. Tian, X. She, H. Yu, L. Shu, and Y. Shi J. Org. Chem. 67 2002 2435
41. L. Shu, P. Wang, Y. Gan, and Y. Shi Org. Lett. 5 2003 293
42. L. Shu, and Y. Shi Tetrahedron Lett. 45 2004 8115
43. M. Hickey, D. Goeddel, Z. Crane, and Y. Shi Proc. Natl. Acad. Sci. U.S.A. 101 2004 5794
44. A.L. Baumstark, and C.J. McCloskey Tetrahedron Lett. 28 1987 3311
45. For leading references on calculation studies, see: (a) R.D. Bach, J.L. Andres, A.L. Owensby, H.B. Schlegel, and J.J.W. McDouall J. Am. Chem. Soc. 114 1992 7207
46. K.N. Houk, J. Liu, N.C. DeMello, and K.R. Condroski J. Am. Chem. Soc. 119 1997 10147
47. C. Jenson, J. Liu, K.N. Houk, and W.L. Jorgensen J. Am. Chem. Soc. 119 1997 12982
48. A. Armstrong, I. Washington, and K.N. Houk J. Am. Chem. Soc. 122 2000 6297
49. D.V. Deubel J. Org. Chem. 66 2001 3790
50. R.F. Brady Carbohydr. Res. 15 1970 35
51. K.H. Aamlid, L. Hough, and A.C. Richardson Carbohydr. Res. 202 1990 117
52. I.I. Cubero, M.T.P. Lopez-Espinosa, A.C. Richardson, and K.H. Aamlid Carbohydr. Res. 242 1993 281
53. A.J. Mancuso, S.-L. Huang, and D. Swern J. Org. Chem. 43 1978 2480
54. R.J. Cregge, J.L. Herrmann, C.S. Lee, J.E. Richman, and R.H. Schlessinger Tetrahedron Lett. 1973 2425
55. Earlier studies suggested that substituents larger than methyl groups could also lower the enantioselectivity, see: Y. Tu, Z.-X. Wang, M. Frohn, M. He, H. Yu, Y. Tang, and Y. Shi J. Org. Chem. 63 1998 8475