Synthesis and Diels–Alder Reaction of Acetylenic Sulfonate†

Abstract

The first synthesis of acetylenic sulfonate and its Diels–Alder reactions are reported.

References

1. W. Curruther, Cycloaddition in Organic Synthesis, Pergamon PressNew York, 1990.
2. A. W. M. Lee, W. H. Chan and M. S. Wong, J. Chem. Soc., Chem. Commun., 1988, 1585.
3. A. W. M. Lee, W. H. Chan, F. Y. Ji and W. H. Poon, J. Chem. Res. (S), 1995, 368.
4. A. W. M. Lee, W. H. Chan and T. T. Chan, J. Chem. Soc., Perkin Trans. 1, 1992, 309, 945; W. H. Chan, A. W. M. Lee and T. Y. Lee, J. Chem. Soc., Perkin Trans 1, 1994, 2355.
5. W. H. Chan, A. W. M. Lee and L. Jiang, Tetrahedron Lett., 1995, 36, 715; A. W. M. Lee, W. H. Chan and T. Mo, Tetrahedron Lett., 1997, 38, 3001.
6. W. H. Chan, A. W. M. Lee and K. M. Lee, J. Chem. Res. (S), 1994, 138.
7. A. W. M. Lee, W. H. Chan, L. S. Jiang and K. W. Poon, Chem. Commun., 1997, 611.
8. K. Tanake, in The Chemistry of Sulphonic Acids, Esters and Their Derivatives, ed. S. Patai and Z. Rappoport, Wiley, New York, 1991, 401.
9. H. Distler, Angew. Chem., Int. Ed. Engl., 1965, 4, 300; L. L. Klein and T. M. Deeb, Tetrahedron Lett., 1985, 26, 3935.
10. P. Metz, M. Fleischer and R. Fröhlich, Tetrahedron, 1995, 51, 711.
11. J. K. Whitesell, Chem. Rev., 1992, 92, 953.
12. J. Kenyon, H. Phillips and F. M. H. Taylor, J. Chem. Soc., 1933, 173; W. Gerrard, J. Kenyon and H. Phillips, J. Chem. Soc., 1937, 153; R. M. Coates and J. P. Chen, Tetrahedron Lett., 1969, 2705.
13. Y. Gao and K. B. Sharpless, J. Am. Chem. Soc., 1988, 110, 7538.