Asymmetric epoxidation using hydrogen peroxide (H2O2) as primary oxidant

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8721-8724

  Shu, Lianhe ^a   Shi, Yian ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HYDROGEN PEROXIDE; KETONE; OXIDIZING AGENT;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; EPOXIDATION; REACTION ANALYSIS;

EID: 0033544829     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01814-6     Document Type: Article

References (43)

1. For general leading references on dioxiranes, see: (a) Murray, R. W. Chem. Rev. 1989, 89, 1187.
2. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
3. (c) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811.
4. (d) Clennan, E. L. Trends in Organic Chemistry 1995, 5, 231.
5. (e) Adam, W.; Smerz, A. K. Bull. Soc. Chim. Belg. 1996, 105, 581.
6. (f) Denmark, S. E.; Wu, Z. Synlett 1999, 847.
7. For selected examples of in situ generation of dioxiranes, see: (a) Curci, R.; Fiorentino, M.; Troisi, L.; Edwards, J. O.; Pater, R. H. J. Org. Chem. 1980, 45, 4758.
8. (b) Gallopo, A. R.; Edwards, J. O. J. Org. Chem. 1981, 46, 1684.
9. (c) Corey, P. F.; Ward, F. E. J. Org. Chem. 1986, 51, 1925.
10. (d) Adam, W.; Hadjiarapoglou, L.; Smerz, A. Chem. Ber. 1991, 124, 227.
11. (e) Kurihara, M.; Ito, S.; Tsutsumi, N.; Miyata, N. Tetrahedron Lett. 1994, 35, 1577.
12. (f) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391.
13. (g) Yang, D.; Wong, M. K.; Yip, Y. C. J. Org. Chem. 1995, 60, 3887.
14. (h) Boehlow, T. R.; Buxton, P. C.; Grocock, E. L.; Marples, B. A.; Waddington, V. L. Tetrahedron Lett. 1998, 39, 1839.
15. (i) Denmark, S. E.; Wu, Z. J. Org. Chem. 1998, 63, 2810 and references cited therein.
16. (j) Frohn, M.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 6425.
17. (k) Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Cheung, K.-K. J. Org. Chem. 1998, 63, 9888 and references cited therein.
18. For leading references on asymmetric epoxidation mediated by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155.
19. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831.
20. (c) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L. Tetrahedron 1995, 51, 3587.
21. (d) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491.
22. (e) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921.
23. (f) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995.
24. (g) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288.
25. (h) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622.
26. (i) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621.
27. (j) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943.
28. (k) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659 and references cited therein.
29. (l)See Ref. 1f.
30. 5).
31. Schulz, M.; Liebsch, S.; Kluge, R.; Adam, W. J. Org. Chem. 1997, 62, 188.
32. For a general reference on hydrogen peroxide, see: Strukul, G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Kluwer Academic Publishers: Dordrecht, 1992.
33. For examples of asymmetric epoxidation mediated by the fructose-derived ketone, see: (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
34. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
35. (c) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 3099.
36. (d) Zhu, Y.; Tu, Y.; Shi, Y. Tetrahedron Lett. 1998, 39, 7819.
37. (a) Payne, G. B.; Deming, P. H.; Williams, P. H. J. Org. Chem. 1961, 26, 659.
38. (b) Payne, G. B. Tetrahedron 1962, 18, 763.
39. (c) McIsaac Jr., J. E.; Ball, R. E.; Behrman, E. J. J. Org. Chem. 1971, 36, 3048.
40. (d) Bach, R. D.; Knight, J. W. Org. Synth. 1981, 60, 63.
41. (e) Arias, L. A.; Adkins, S.; Nagel, C. J.; Bach, R. D. J. Org. Chem. 1983, 48, 888.
42. 2CN, t-BuCN and PhCN were used.
43. 3N in hexane, using hexane:ether 1:0-50:1 as eluent) to afford the epoxide product as a colorless oil (0.113 g, 84% yield, 92% ee).