Convenient synthesis of 2-alkynyl-cyclopropanes and -oxiranes

Abstract

Addition of nucleophiles such as dimethylsulfoxonium methylide and Bu^tOOLi to the conjugate enyne sulfones 4–7, 11–14, 27–28 and 31 occurs at the β-position to the phenylsulfonyl group to give the corresponding cyclopropanes 15–17 and 19–22 and the oxiranes 33–38 in high yields. The thermal reactions of vinyloxirane 36 show an oxy-Cope rearrangement to give 2-phenylsulfonylphenol 39.

References

1. (a) M. Yoshimatsu, M. Kawahigashi, H. Shimizu and T. Kataoka, J. Chem. Soc., Chem. Commun., 1995, 583; M. Yoshimatsu, M. Hayashi, G. Tanabe and O. Muraoka, Tetrahedron Lett., 1996, 37, 4161; (b) M. Hohmann and N. Krause, Chem. Ber., 1995, 128, 851.
2. M. Yoshimatsu and J. Hasegawa, Tetrahedron Lett., 1996, 37, 7381; M. Yoshimatsu and J. Hasegawa, J. Chem. Soc., Perkin Trans. 1, 1997, 211.
3. D. B. Reddy, P. S. Reddy, B. V. Reddy and P. A. Reddy, Synthesis, 1987, 74; J. E. Boeckvall, C. Loefstroem, S. K. Juntunen and M. Mattson, Tetrahedron Lett., 1993, 34, 2007.
4. K. Ogura, T. Yahata, K. Takahashi and H. Iida, Tetrahedron Lett., 1983, 24, 5761; K. Ogura, T. Iihama, K. Takahashi and H. Iida, Tetrahedron lett., 1984, 25, 2671.
5. A. G. Hartmann and R. L. Harris, J. Am. Chem. Soc., 1971, 93, 2471.
6. J. G. Hill, B. E. Rossiter and K. B. Sharpless, J. Org. Chem., 1983, 48, 3607; R. Curci and F. DiFuria, Tetrahedron Lett., 1974, 4085; C. Clark, P. Harmans, O. Meth-Cohn, C. Moore, H. C. Taljaard and G. Vuuren, J. Chem. Soc., Chem. Commun., 1986, 1378; C. T. Hawkin, R. F. W. Jackson and W. Clegg, Tetrahedron Lett., 1988, 29, 4889.
7. N. Manisse and J. Chuche, Tetrahedron, 1977, 33, 2399; W. Eberbach, G. Koenig and U. Trostmann, Tetrahedron Lett., 1979, 4649; W. Eberbach and U. Trostmann, Chem. Ber., 1985, 118, 4035; W. Eberbach and J. Roser, Tetrahedron Lett., 1987, 28, 2685.
8. J. A. Marshall and V. H. Audia, J. Org. Chem., 1987, 52, 1106; B. M. Trost and S. R. Angle, J. Am. Chem. Soc., 1985, 107, 6123; B. M. Trost and G. A. Molander, J. Am. Chem. Soc., 1981, 103, 5969; J. Tsuji, H. Kataoka and Y. Kobayashi, Tetrahedron Lett., 1981, 22, 2575; T. Tsuda, M. Tokai, T. Ishida and T. Saegusa, J. Org. Chem., 1986, 51, 5216.
9. F. Bourelle-Wargnier, M. Vincent and J. Chuche, J. Org. Chem., 1980, 45, 428.
10. Structure Solution Methods: MITHRIL; C. J. Gilmore, MITHRIL—an integrated direct methods computer program, University of Glasgow, Scotland, J. Appl. Crystallogr., 1984, 17, 42; DIRDIF: P. T. Beurskens, DIRDIF: Direct Methods for Different Structures—an automatic procedure for phase extension and refinement of difference structure factors. Technical Report 1984/1 Crystallography Laboratory, Toernooiveld, 6525 Ed. Nijmegen, Netherlands.