Hydrozirconation of alkynyl(phenyl)iodonium salts and stereoselective synthesis of (E )-trisubstituted olefins

Abstract

Hydrozirconation of alkynyl(phenyl)iodonium salts affords alkenylchlorozirconocenes with the Zr-C bond germinal to the iodonium moiety, and two subsequent substitution reactions proceed with retention of the configuration of the carbon-carbon double bond.

References

1. Recent reviews: (a) P. J. Stang, Angew. Chem., Int. Ed. Engl., 1992, 31, 274; (b) P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123.
2. Reviews: (a) J. Schwartz and J. A. Labinger, Angew. Chem., Int. Ed. Engl., 1976, 15, 333; (b) J. A. Labinger, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 8, p. 667; (c) P. Wipf and H. Jahn, Tetrahedron, 1996, 52, 12853; (d) E. Negishi and T. Takahashi, Synthesis, 1988, 1.
3. M. Ochiai, K. Sumi, Y. Takaoka, M. Kunishima, Y. Nagao, M. Shiro and E. Fujita, Tetrahedron, 1988, 44, 4095.
4. D. W. Hart, T. F. Blackburn and J. Schwartz, J. Am. Chem. Soc., 1975, 97, 679.
5. M. Yoshifuji, M. J. Loots and J. Schwartz, Tetrahedron Lett., 1977, 1303.
6. For the preparation of alkynyliodonium salts, see ref. 1c and references cited therein.
7. S. L. Buchwald, S. L. LaMaire, R. B. Nielsen, B. T. Watson and M. S. King, Tetrahedron Lett., 1987, 28, 3895.
8. (a) T. Kitamura and P. J. Stang, J. Org. Chem., 1988, 53, 4105; (b) P. J. Stang, B. W. Surber, Z. C. Chen, K. A. Roberts and A. G. Anderson, J. Am. Chem. Soc., 1987, 109, 228.
9. C. R. Johnson and G. A. Dutra, J. Am. Chem. Soc., 1973, 95, 7777.
10. J. Klein and R. Levene, Tetrahedron Lett., 1974, 2935.
11. A. Pross and S. Sternhell, Aust. J. Chem., 1970, 23, 989.
12. R. H. Smithers, J. Org. Chem., 1978, 43, 2833.
13. M. S. Baird and C. B. Reese, Synthesis, 1976, 385.
14. P. J. Kropp and S. D. Crawford, J. Org. Chem., 1994, 59, 3102.
15. T. N. Mitchell, R. Wickenkamp, A. Amamria, R. Dicke and U. Schneider, J. Org. Chem., 1987, 52, 4868.