Asymmetric dihydroxylation of allylic phosphine oxides

(Note: The full text of this document is currently only available in the PDF Version )

Adam Nelson and Stuart Warren


Abstract

Diphenylphosphinoyl diols have been produced by asymmetric dihydroxylation (AD) of allylic phosphine oxides and have been shown to be useful synthetic intermediates. The results of this study are discussed in terms of the model which has been proposed by Sharpless to explain the enantioselectivity of his AD reaction. The dihydroxylation results are thus of both mechanistic and synthetic value.


References

  1. J. Clayden, A. B. McElroy and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1995, 1913 RSC.
  2. J. Clayden and S. Warren, Angew. Chem., Int. Ed. Engl., 1996, 35, 241 CrossRef CAS.
  3. H. C. Kolb, M. S. VanNieuwenhze and K. B. Sharpless, Chem. Rev., 1994, 94, 2483 CrossRef CAS.
  4. Preliminary communication: A. Nelson, P. O'Brien and S. Warren, Tetrahedron Lett., 1995, 36, 2685 Search PubMed.
  5. (a) H. C. Kolb, P. G. Andersson and K. B. Sharpless, J. Am. Chem. Soc., 1994, 116, 1278 CrossRef CAS; (b) P.-O. Norrby, H. C. Kolb and K. B. Sharpless, J. Am. Chem. Soc., 1994, 116, 8470 CrossRef CAS; (c) E. J. Corey and M. C. Noe, J. Am. Chem. Soc., 1996, 118, 11038 CrossRef CAS.
  6. A. Nelson and S. Warren, Tetrahedron Lett., 1996, 37, 1501 CrossRef CAS.
  7. (a) G. Chelucci, M. A. Cabras, C. Botteghi and M. Marchetti, Tetrahedron: Asymmetry, 1994, 5, 299 CrossRef CAS; (b) C. Basoli, C. Botteghi, M. A. Cabras, G. Chelucci and M. Marchetti, J. Organomet. Chem., 1995, 488, C20 CrossRef CAS.
  8. (a) S. K. Armstrong, E. W. Collington, J. G. Knight, A. Naylor and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1993, 1433 RSC; (b) N. Feeder, G. Hutton and S. Warren, Tetrahedron Lett., 1994, 35, 5911 CrossRef CAS.
  9. M. P. Savage and S. Trippett, J. Chem. Soc. C, 1966, 1842 RSC.
  10. (a) L. Duhamel, S. Fouquay and J.-C. Plaquevent, Tetrahedron Lett., 1986, 27, 4975 CrossRef CAS; (b) E. Vedejs, N. Lee and S. T. Sakata, J. Am. Chem. Soc., 1994, 116, 2175 CrossRef CAS; (c) K. Ishihara, M. Kaneeda and H. Yamamoto, J. Am. Chem. Soc., 1994, 116, 11179 CrossRef CAS; (d) F. Cavelier, S. Gomez, R. Jacquier and J. Verducci, Tetrahedron: Asymmetry, 1993, 4, 2501 CrossRef CAS.
  11. (a) E. Vedejs and J. A. Garcia-Rivas, J. Org. Chem., 1994, 59, 6517 CrossRef CAS; (b) P. O'Brien and S. Warren, Synlett, 1996, 579 CrossRef CAS.
  12. T. D. Nelson and A. I. Meyers, Tetrahedron Lett., 1994, 35, 3259 CrossRef CAS.
  13. (a) R. I. Johnson and J. Kenyon, J. Chem. Soc., 1932, 722 Search PubMed; (b) J. A. Katzenellenbogen and A. L. Crumrine, J. Am. Chem. Soc., 1976, 98, 4925 CrossRef CAS; (c) T. Harada, H. Kurokawa, Y. Kagamihara, S. Tanaka, A. Inoue and A. Oku, J. Org. Chem., 1992, 57, 1412 CrossRef CAS; (d) J. Colonge and J. C. Brunie, Bull. Soc. Chim. Fr., 1963, 42 CAS; (e) C. S. Marvel and R. G. Woolford, J. Org. Chem., 1958, 23, 1658 CrossRef CAS.
  14. (a) W. C. Still and A. Mitra, J. Am. Chem. Soc., 1978, 100, 1927 CrossRef CAS; (b) K.-K. Chan and G. Saucy, J. Org. Chem., 1977, 42, 3828 CrossRef CAS; (c) G. Büchi, M. Cushman and H. Wüest, J. Am. Chem. Soc., 1974, 96, 5563 CrossRef CAS.
  15. E. C. Ashby, R. Gurumurthy and R. W. Ridlehuber, J. Org. Chem., 1993, 58, 5932.
  16. M. R. Binns, R. K. Haynes, A. G. Katsifis, P. A. Schober and S. C. Vonwiller, J. Am. Chem. Soc., 1988, 110, 5411 CrossRef CAS.
  17. 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, 57, 2768 CrossRef CAS.
  18. J. Eames, H. J. Mitchell, A. Nelson, P. O'Brien, S. Warren and P. Wyatt, Tetrahedron Lett., 1995, 36, 1719 CrossRef CAS.
  19. Lewis basic groups are well known to direct osmylations by coordination to osmium tetroxide: (a) F. M. Hauser, S. R. Ellenberger, J. C. Clardy and L. S. Bass, J. Am. Chem. Soc., 1984, 106, 2458 CrossRef CAS; (b) S. B. King and B. Ganem, J. Am. Chem. Soc., 1991, 113, 5089 CrossRef CAS; (c) A. C. Peterson and J. M. Cook, Tetrahedron Lett., 1994, 5, 2651 CrossRef CAS.
  20. W. H. Pirkle, D. L. Sikkenga and M. S. Pavlin, J. Org. Chem., 1977, 42, 384 CrossRef CAS.
  21. (a) P. O'Brien and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1996, 2117 RSC; (b) P. O'Brien and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1996, 2129 RSC.
  22. J. Ukai, Y. Ikeda, N. Ikeda and H. Yamamoto, Tetrahedron Lett., 1983, 24, 4029 CrossRef CAS.
  23. A. Bell, A. H. Davidson, C. Earnshaw, H. K. Norrish, R. S. Torr, D. B. Trowbridge and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1983, 2879 RSC.
  24. S. Okamoto, K. Tani, F. Sato, K. B. Sharpless and D. Zargarian, Tetrahedron Lett., 1993, 34, 2509 CrossRef CAS.
  25. E. N. Jacobsen, I. Markó, W. S. Mungall, G. Schröder and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 1968 CrossRef CAS.
  26. (a) J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543 CrossRef CAS; (b) Y. Goldberg and H. Alper, J. Org. Chem., 1992, 57, 3731 CrossRef CAS; (c) D. E. Ward and C. K. Rhee, Tetrahedron Lett., 1991, 32, 7165 CrossRef CAS.
  27. L. Wang and K. B. Sharpless, J. Am. Chem. Soc., 1992, 114, 7568 CrossRef CAS.
  28. H. C. Kolb, P. G. Andersson and K. B. Sharpless, J. Am. Chem. Soc., 1994, 116, 1278 CrossRef CAS.
  29. (a) A. D. Buss, W. B. Cruse, O. Kennard and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1984, 243 RSC; (b) A. D. Buss, S. Warren, J. S. Leake and G. H. Whitham, J. Chem. Soc., Perkin Trans. 1, 1983, 2215 RSC; (c) N. J. S. Harmat and S. Warren, Tetrahedron Lett., 1990, 31, 2743 CrossRef CAS.
  30. J. Clayden, A. Nelson and S. Warren, Tetrahedron Lett., 1997, 38, 3471 CrossRef CAS.
  31. J. Park and S. F. Petersen, J. Org. Chem., 1990, 55, 5924 CrossRef CAS.
  32. (a) N. Tanno and S. Terashima, Chem. Pharm. Bull., 1983, 31, 837 CAS; (b) D. Seebach, G. Crass, E.-M. Wilka, D. Hilvert and E. Brunner, Helv. Chim. Acta, 1979, 62, 2695 CrossRef CAS.
  33. V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda and K. B. Sharpless, J. Am. Chem. Soc., 1981, 103, 6237 CrossRef CAS.
  34. (a) Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765 CrossRef CAS; (b) B. E. Rossiter, Synthetic Aspects and Applications of Asymmetric Epoxidation, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, 1985, vol. 5, ch. 7, p. 193 Search PubMed.
  35. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1932, 722.
  36. H. Suzuki, A. Tanaka and K. Yamashitu, Agric. Biol. Chem., 1987, 51, 3369 CAS.
  37. A. Kumar and D. C. Dittmer, Tetrahedron Lett., 1994, 35, 5583 CrossRef CAS.