Vanadium-catalyzed asymmetric epoxidation of allylic alcohols mediated by (+)-norcamphor-derived hydroperoxide

European Journal of Organic Chemistry

Volumn , Issue 8, 2005, Pages 1669-1674

  Lattanzi, Alessandra ^a   Piccirillo, Sandro ^a   Scettri, Arrigo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

Asymmetric synthesis; Diastereoselectivity; Epoxidation; Kinetic resolution; Optically pure hydroperoxides; Vanadium

Indexed keywords

EID: 18144381979     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400736     Document Type: Article

References (41)

1. R. A. Johnson, K. B. Sharpless, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000, p. 231.
2. T. Katsuki, K.B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976.
3. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765-5780.
4. R. C. Michaelson, R.E. Palermo, K. B. Sharpless, J. Am. Chem. Soc. 1977, 99, 1990-1992.
5. K. B. Sharpless, T. R. Verhoeven, Aldrichimica Acta 1979, 12, 63-74.
6. N. Murase, Y. Hoshino, M. Oishi, H. Yamamoto, J. Org. Chem. 1999, 64, 338-339.
7. Y. Hoshino, N. Murase, M. Oishi, H. Yamamoto, Bull. Chem. Soc. Jpn. 2000, 73, 1653-1658.
8. Y. Hoshino, H. Yamamoto, J. Am. Chem. Soc. 2000, 122, 10452-10453.
9. C. Bolm, T. Kühn, Synlett 2000, 6, 899-901.
10. H.-L. Wu, B.-J. Uang, Tetrahedron: Asymmetry 2002, 13, 2625-2628.
11. B. Traber, Y.-G. Jung, T. K. Park, J.-I. Hong, Bull. Korean Chem. Soc. 2001, 22, 547-548.
12. W. Adam, A. K. Beck, A. Pichota, C. R. Saha-Möller, D. Seebach, N. Vogl, R. Zhang, Tetrahedron: Asymmetry 2003, 14, 1355-1361.
13. M. G. Finn, K. B. Sharpless, Asymmetrie Synthesis Academic Press, New York, 1985, p. 247.
14. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765-5780.
15. P. Pitchen, E. Duñach, M. N. Deshmukh, H. B. Kagan, J. Am. Chem. Soc. 1984, 106, 8188-8193.
16. H.-J. Hamann, E. Höft, D. Mostowicz, A. Mishnev, Z. Urbańczyk-Lipkowska, M. Chmielewski, Tetrahedron 1997, 53, 185-192.
17. D. Mostowicz, M. Jurczak, H.-J. Hamann, E. Höft, M. Chmielewski, Eur. J. Org. Chem. 1998, 11, 2617-2621.
18. W. Adam, M. N. Korb, K. J. Roschmann, C. R. Saha-Möller, J. Org. Chem. 1998, 63, 3423-3428.
19. W. Adam, P. L. Alsters, R. Neumann, C. R. Saha-Möller, D. Seebach, A. K. Beck, R. Zhang, J. Org. Chem. 2003, 68, 8222-8231.
20. A. Lattanzi, P. Iannece, A. Vicinanza, A. Scettri, Chem. Commun. 2003, 1440-1441.
21. A. Lattanzi, P. Iannece, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 1779-1785.
22. A. Lattanzi, P. Iannece, A. Scettri, Tetrahedron: Asymmetry 2004, 15, 413-418.
23. K. P. Bryliakov, E. P. Talsi, T. Kühn, C. Bolm, New J. Chem. 2003, 27, 609-614.
24. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
25. K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136-4137.
26. [8] at a V/ligand ratio of 1:1.5, a B/A ratio of 95:5 was determined (see Figure 3).
27. R. M. Coates, S. J. Firsan, J. Org. Chem. 1986, 51, 5198-5209.
28. R. V. Huffman, N. K. Nayyar, J. Org. Chem. 1994, 59, 3530-3539.
29. H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249-330.
30. [29].
31. [5]
32. [33]
33. V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, K. B. Sharpless, J. Am. Chem. Soc. 1981, 103, 6237-6240.
34. W. Adam, B. Nestler, Tetrahedron Lett. 1993, 34, 611-614.
35. W. Adam, T. Wirth, Acc. Chem. Res. 1999, 32, 703-710.
36. At the end of the epoxidation reactions, alcohol 6 was isolated by flash chromatography in 80-90% yield and recycled for the one-step synthesis of 2.
37. D. E. Robinson, M. D. Holladay, Org. Lett. 2000, 2, 2777-2779.
38. J. A. Warshaw, D. E. Gallis, B. J. Acken, O. J. Gonzalez, D. R. Crist, J. Org, Chem. 1989, 54, 1736-1743.
39. M. Couturier, J. L. Thicker, C. Proulx, G. Boucher, P. Dubé, B. M. Andresen, A. Ghosh, J. Org. Chem. 2002, 67, 4833-4838.
40. R. V. Huffman, N. K. Nayyar, W. Chen, J. Org. Chem. 1992, 57, 5700-5707.
41. W. Adam, P. L. Alsters, R. Neumann, C. R. Saha-Möller, D. Seebach, R. Zhang, Org. Lett. 2003, 5, 725-728.