Efficient synthesis of chrysanthemate precursor from chiral p-tolyl β-(trimethylsilyl)ethyl sulfoxide

Abstract

Reaction of α-lithio-β-silylethyl sulfoxide with ethyl 4-bromo- or 4-chloro-4-methylpent-2-enoate gives the cyclopropanecarboxylate as a single diastereomer which is converted to (1R)-trans-2-formyl-3,3-dimethylcyclopropanecarboxylate in high overall yield.

References

1. For reviews, see (a) D. Arlt, M. Jautelat and R. Lantzsch, Angew. Chem., Int. Ed. Engl., 1981, 20, 703; (b) J. Salaün, Chem. Rev., 1989, 89, 1247.
2. For recent reviews, see (a) V. K. Singh, A. DattaGupta and G. Sekar, Synthesis, 1997, 137; (b) M. P. Doyle and M. N. Protopopova, Tetrahedron, 1998, 54, 7919.
3. (a) R. E. Lowenthal, A. Abiko and S. Masamune, Tetrahedron Lett., 1990, 31, 6005; (b) R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 1991, 32, 7373.
4. W. A. Kleschick, M. W. Reed and J. Bordner, J. Org. Chem., 1987, 52, 3168.
5. T. Toru, S. Nakamura, H. Takemoto and Y. Ueno, Synlett, 1997, 5, 449.
6. S. Kusuda, Y. Ueno and T. Toru, Tetrahedron, 1994, 50, 1045.
7. (a) J. H. Babler and A. J. Tortorello, J. Org. Chem., 1976, 41, 885; (b) P. R. O. Montellano and S. E. Dinizo, J. Org. Chem., 1978, 43, 4323.
8. (a) M. J. Devos, L. Hevesi, P. Bayet and A. Krief, Tetrahedron Lett., 1976, 3911; (b) W. G. Taylor, Synthesis, 1980, 554; (c) M. Fujita, T. Hiyama and K. Kondo, Tetrahedron Lett., 1986, 27, 2139; (d) H. Tanaka, S. Yamashita, M. Yamanoue and S. Torii, J. Org. Chem., 1989, 54, 444.