Enantioselective epoxidation of nonconjugated cis-olefins by chiral dioxirane

Organic Letters

Volumn 11, Issue 22, 2009, Pages 5150-5153

  Burke, Christopher P ^a   Shi, Yian ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; DIOXIRANE; EPOXIDE; KETONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROPHOBICITY; STEREOISOMERISM; SYNTHESIS;

ALKENES; EPOXY COMPOUNDS; HYDROPHOBICITY; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 70749110706     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901724v     Document Type: Article

References (62)

1. For leading reviews, (a) Denmark, S. E.; Wu, Z. Synlett 1999, 847.
2. (b) Frohn, M.; Shi, Y. Synthesis 2000, 1979.
3. (c) Shi, Y. Acc. Chem. Res. 2004, 37. 488.
4. (d) Yang, D. Acc. Chem. Res. 2004, 37, 497.
5. (e) Wong, O. A.; Shi, Y. Chem. Rev. 2008, 108, 3958.
6. (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
7. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
8. (c) Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
9. (a) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000. 122, 11551.
10. (b) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929.
11. (c) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435.
12. (d) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293.
13. (e) Shu, L.; Shi, Y. Tetrahedron Lett. 2004, 45, 8115.
14. (f) Goeddel, D.; Shu, L.; Yuan, Y.; Wong, O. A.; Wang, B.; Shi, Y. J. Org. Chem. 2006, 71, 1715.
15. (g) Wong, O. A.; Shi, Y. J. Org. Chem. 2006, 71, 3973.
16. (h) Shen, Y.-M.; Wang, B.; Shi, Y. Angew. Chem., Int. Ed. 2006, 45, 1429.
17. Shen. Y.-M.; Wang, B.; Shi, Y. Tetrahedron Lett. 2006, 47, 5455.
18. (j) Wang, B.; Shen, Y.-M.; Shi, Y. J. Org. Chem. 2006, 71, 9519.
19. (k) Burke, C. P.; Shi, Y. Angew. Chem., Int. Ed. 2006, 45, 4475.
20. (l) Burke, C. P.; Shi, Y. J. Org. Chem. 2007, 72, 4093.
21. (m) Burke, C. P.; Shi, Y. J. Org. Chem. 2007, 72, 6320.
22. For leading reviews on metal-catalyzed asymmetric epoxidation of unfunctionalized olefins, (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH; New York, 1993; Chapter 4.2.
23. (b) Coliman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404.
24. (c) Mukaiyama, T. Aldrichim. Acta 1996, 29, 59.
25. (d) Katsuki, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH; New York, 2000; Chapter 6B.
26. (e) McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563.
27. (f) Xia, Q.-H.; Ge, H.-Q.; Ye, C-P.; Liu, Z.-M.; Su, K.-X. Chem. Rev. 2005, 105, 1603.
28. (g) Barlan, A. U.; Zhang, W.; Yamamoto, H. Tetrahedron 2007, 63, 6075.
29. (h) Matsumoto, K.; Sawada, Y.; Katsuki, T. Pure Appl. Chem. 2008, 80, 1071.
30. For leading references on metal- and enzyme-catalyzed asymmetric epoxidation of nonconjugated cis-olefins, (a) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
31. (b) Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martinez, L. E. Tetrahedron 1994, 50, 4323.
32. (c) Hamada, T.; Irie, R.; Katsuki, T. Synlett 1994, 479.
33. (d) Mikame, D.; Hamada, T.; Irie, R.; Katsuki, T. Synlett 1995, 827.
34. (e) Sawada, Y.; Matsumoto, K.; Katsuki, T. Angew. Chem., Int. Ed. 2007, 46, 4559.
35. (f) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415.
36. 94% ee has been obtained for 3,3-ethylenedioxycyclohexene with chiral (salen)Mn(III) catalyst; see refs 5a and 5b.
37. For a recent report on Ti-catalyzed asymmetric epoxidation of nonactivated ci's-olefins (70-97% ee), see ref 5e.
38. (a) Asami, M.; Kanemaki, N. Tetrahedron Lett. 1989, 30, 2125.
39. (b) Utaka, M.; Konishi, S.; Takeda, A. Tetrahedron Lett. 1986, 27, 4737.
40. (c) Zaks, A.; Dodds, D. R. J. Am. Chem. Soc. 1995, 117, 10419.
41. For leading references on asymmetric epoxidation of allylic and homoallylic alcohols, (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1.
42. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH; New York, 2000; Chapter 6A.
43. (c) Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 44, 4389.
44. (d) Zhang, W.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 286.
45. For entry 5, the epoxide did not completely cyclize under the reaction conditions; a mixture of epoxy acid and lactone were isolated from the crude reaction mixture. Refluxing this crude mixture overnight in cyclohexane gave the lactone product in overall 88% yield; see; Ochiai, M.; Ukita, T.; Iwaki, S.; Nagao, Y.; Fujita, E. J. Org. Chem. 1989, 54, 4832.
46. For leading references, (a) Gräfe, U.; Reinhardt, G.; Schade, W.; Krebs, D.; Eritt, I.; Fleck, W. F.; Hienrich, E.; Radics, L. J. Antibiot. 1982, 35, 609.
47. (b) Gräfe, U.; Eritt, I. J. Antibiot. 1983, 36, 1592.
48. (c) Cooper, R. D.; Jigajinni, V. B.; Wightman, R. H. Tetrahedron Lett. 1984, 45, 5215.
49. (d) Mori, K.; Otsuka, T. Tetrahedron 1985, 41, 3253.
50. (e) Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun. 1985, 1636.
51. (f) Fujisawa, T.; Kojima, E.; Itoh, T.; Sato, T. Chem. Lett. 1985, 1751.
52. (g) Kotsuki, H.; Kadota, I.; Ochi, M. J. Org. Chem. 1990, 55, 4417.
53. (h) Wang, Z.-M.; Zhang, X.-L.; Sharpless, K. B.; Sinha, S. C.; Sinha-Bagchi, A.; Keinan, E. Tetrahedron Lett. 1992, 33, 6407.
54. (a) Kanerva, L. T.; Vänttinen, E. Tetrahedron: Asymmetry 1993, 4, 85.
55. (b) Yu, L.; Wang, Z. J. Chem. Soc., Chem. Commun. 1993, 232.
56. (c) Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2005, 4389-4444
57. (a) Reference.9d (b) Chiappe, C.; Cordoni, A.; Lo Moro, G.; Palese, C. D. Tetrahedron: Asymmetry 1998, 9, 341.
58. (c) Ikegami, S.; Katsuki, T.; Yamaguchi, M. Chem. Lett. 1987, 83.
59. Sala, L. F.; Cravero, R. M.; Signorella, S. R.; González-Sierra, M.; Rúveda, E. A. Synth. Commun. 1987, 17, 1287.
60. (a) Gayet, A.; Bertilsson, S.; Andersson, P. G. Org. Lett. 2002, 4, 3777.
61. (b) Gayet, A.; Andersson, P. G. Tetrahedron Lett. 2005, 46, 4805.
62. It was found that ketone 2a was the most effective catalyst. No ee was obtained with ketone 2b, and 14% ee of the opposite enantiomer was obtained with ketone 2c for cis-1-methoxy-2-nonene using DME/DMM (3:1, v/v) as solvent.