Asymmetric epoxidation and kinetic resolution of allylic phosphine oxides

Abstract

Allylic alcohols bearing a diphenylphosphinoyl group undergo asymmetric epoxidation with excellent enantioselectivity, and can undergo kinetic resolution with good diastereoselectivity, with the diphenylphosphinoyl group exerting an anti-directing effect on the epoxidation.

References

1. (a) A. B. McElroy and S. Warren, Tetrahedron Lett., 1985, 26, 5709; (b) J. Clayden, E. W. Collington and S. Warren, Tetrahedron Lett., 1993, 34, 1327; (c) J. Clayden, E. W. Collington, R. B. Lamont and S. Warren, Tetrahedron Lett., 1993, 34, 2203.
2. (a) J. Clayden, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, preceding paper; (b) A. B. McElroy and S. Warren, Tetrahedron Lett., 1985, 26, 2119.
3. Preliminary communication: J. Clayden, E. W. Collington and S. Warren, Tetrahedron Lett., 1992, 33, 7043.
4. (a) T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974; (b) V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda and K. B. Sharpless, J. Am. Chem. Soc., 1981, 103, 6237; (c) Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765.
5. (a) P. S. Brown, A. B. McElroy and S. Warren, Tetrahedron Lett., 1985, 26, 249; (b) P. S. Brown, N. Greeves, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1991, 1485.
6. (a) J. Clayden, E. W. Collington and S. Warren, Tetrahedron Lett., 1992, 33, 7039; (b) J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1993, 2913.
7. (a) M. G. Finn and K. B. Sharpless, in Asymmetric Synthesis, Academic Press, ( 1985), ed. Morrison, J. D., vol. 5, ch. 8;; (b) B. E. Rossiter, in Asymmetric Synthesis, Academic Press, ( 1985), ed. Morrison, J. D., vol. 5, ch. 7, p. 212;; (c) R. A. Johnson and K. B. Sharpless, in Comprehensive Organic Synthesis, Pergamon( 1992), ed. B. Trost and I. Fleming, vol. 7, ch. 3.2..
8. J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543.
9. W. H. Pirkle, D. L. Sikkenga and M. S. Pavlin, J. Org. Chem., 1977, 42, 384.
10. J. Clayden, E. W. Collington, J. Elliott, S. J. Martin, A. B. McElroy, S. Warren and D. Waterson, J. Chem. Soc., Perkin Trans. 1, 1993, 1849.
11. S. Masamune, W. Choy, J. S. Petersen and L. R. Sita, Angew. Chem., Int. Ed. Engl., 1985, 24, 1.
12. (a) K. B. Sharpless, C. H. Behrens, T. Katsuki, A. W. M. Lee, V. S. Martin, M. Takatani, S. M. Viti, F. J. Walker and S. S. Woodard, Pure Appl. Chem., 1983, 55, 589; (b) B. E. Rossiter, T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1981, 103, 464; (c) M. J. Schweiter and K. B. Sharpless, Tetrahedron Lett., 1985, 26, 2543.
13. B. H. McKee, T. H. Kalantar and K. B. Sharpless, J. Org. Chem., 1991, 56, 6966.
14. We are very grateful to Dr. R. B. Lamont for determining the crystal structures depicted in this paper..
15. J. Clayden, A. B. McElroy and S. Warren, manuscript in preparation..
16. A. S. Narula, Tetrahedron Lett., 1981, 22, 2017.
17. I. Fleming, J. Chem. Soc., Perkin Trans. 1, 1992, 3363 and references therein..
18. S. S. Woodard, M. G. Finn and K. B. Sharpless, J. Am. Chem. Soc., 1991, 113, 106.
19. J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, in the press; J. Clayden and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1994, 1529.
20. (a) S. Takano, Y. Iwabuchi and K. Ogasawara, Synlett., 1991, 548; (b) S. Takano, Y. Iwabuchi and K. Ogasawara, J. Am. Chem. Soc., 1991, 113, 2786.