An efficient protocol for Sharpless-style racemic dihydroxylation

Abstract

Racemic dihydroxylation of alkenes is efficiently accomplished with catalytic osmium (added as OsCl₃), stoichiometric K₃Fe(CN)₆ and quinuclidine under conditions similar to those of the Sharpless asymmetric hydroxylation.

References

1. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 37, 2768.
2. S. Warren, P. Wyatt, M. McPartlin and T. Woodroffe, Tetrahedron Lett., 1996, 37, 5609.
3. S. Warren and P. Wyatt, Tetrahedron: Asymmetry, 1996, 7, 989.
4. W. H. Pirkle, D. L. Sikkenga and M. S. Pavlin, J. Org. Chem., 1977, 42, 384.
5. V. VanRheenen, R. C. Kelly and D. Y. Cha, Tetrahedron Lett., 1976, 1973.
6. M. S. VanNiewenhze and K. B. Sharpless, J. Am. Chem. Soc., 1993, 115, 7864.
7. K. Morikawa and K. B. Sharpless, Tetrahedron Lett., 1993, 34, 5575.
8. A. Gypser, D. Michel, D. S. Nirschl and K. B. Sharpless, J. Org. Chem., 1998, 63, 7322.
9. E. N. Jacobsen, I. Markó, W. S. Mungall, G. Schröder and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 1968.
10. M. Minato, K. Yamamoto and J. Tsuji, J. Org. Chem., 1990, 55, 766.
11. Footnote 6 in reference 9.
12. J. E. McMurry, M. P. Fleming, K. L. Kees and L. R. Krepski, J. Org. Chem., 1978, 42, 3255.
13. H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2438.
14. M. G. Stockdale, S. Ramurthy and M. J. Miller, J. Org. Chem., 1998, 63, 1221.
15. B. M. Trost and C. B. Lee, J. Am. Chem. Soc., 1998, 120, 6818.
16. S. P. Bew and D. W. Knight, Chem. Commun., 1996, 1007.
17. J.-P. Surivet and J.-M. Vatèle, Tetrahedron Lett., 1996, 37, 4373.
18. R. Rodríguez and F. Bermejo, Tetrahedron Lett., 1996, 37, 5581.
19. S. H. Kang, G. T. Kim and Y. S. Yoo, Tetrahedron Lett., 1997, 38, 603.
20. J.-P. Surivet, J. Gore and J.-M. Vatèle, Tetrahedron, 1996, 52, 14877.
21. C. A. Bewley, H. He, D. H. Williams and D. J. Faulkner, J. Am. Chem. Soc., 1996, 118, 4314.
22. A. J. F. Edmunds and W. Trueb, Tetrahedron Lett., 1997, 38, 1009.
23. A. Nelson, P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 2685.
24. L. Djakovitch, J. Eames, R. V. H. Jones, S. McIntyre and S. Warren, Tetrahedron Lett., 1995, 36, 1723.
25. P. Brownbridge and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1976, 2125.
26. P. J. Walsh, P. Tong Ho, S. B. King and K. B. Sharpless, Tetrahedron Lett., 1994, 35, 5129.
27. N. J. S. Harmat and S. Warren, Tetrahedron Lett., 1990, 31, 2743.
28. H. J. Mitchell and S. Warren, Tetrahedron Lett., 1996, 37, 2105.
29. J. Clayden, E. W. Collington, E. Egert, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 2801.
30. J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 2811.
31. L. Manzoni, T. Pilati, G. Poli and C. Scolastico, J. Chem. Soc., Chem. Commun., 1992, 1027.
32. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
33. T. R. Kelly, Q. Li and V. Bhushan, Tetrahedron Lett., 1990, 31, 161.
34. H. D. Law, J. Chem. Soc., 1906, 89, 1512.
35. G. R. Weisman, J. L. Toner, T. L. Tarnowski, Y. Chao, J. M. Mayer and D. J. Cram, J. Am. Chem. Soc., 1979, 101, 4928.
36. I. I. Lapkin, T. N. Povarnitsyna and L. A. Kostareva, Zh. Obshch. Khim., 1969, 39, 1460.
37. C. N. Barry and S. A. Evans, J. Org. Chem., 1983, 48, 2825.
38. C. Venturello and M. Gambaro, Synthesis, 1989, 295.
39. P. G. Gassman and C. K. Harrington, J. Org. Chem., 1984, 49, 2258.
40. P. F. Cann, D. Howells and S. Warren, J. Chem. Soc., Perkin Trans. 2, 1972, 304.
41. H. Redlich and B. Schneider, Liebigs Ann. Chem., 1983, 412.