Catalytic asymmetric sulfimidation of 1,3-dithianes

Abstract

A direct catalytic sulfimidation of 1,3-dithianes to the corresponding chiral monosulfimides with N-( p-tolylsulfonyl)imino(phenyl)iodinane (TsN[double bond, length half m-dash]IPh) using a catalytic amount of copper(I) triflate (CuOTf ) and a chiral 4,4′-disubstituted bis(oxazoline) as ligand has been developed. The reaction affords the chiral monosulfimides in good yield and with moderate enantioselectivity (up to 40% ee).

References

1. (a) P. C. B. Page, M. J. McKenzie and D. R. Buckle, J. Chem. Soc., Perkin Trans. 1, 1995, 2673; (b) P. C. B. Page and E. S. Namwindwa, Synlett, 1991, 80; (c) P. C. B. Page, E. S. Namwindwa, S. S. Klair and D. Westwood, Synlett, 1990, 457; (d) P. C. B. Page, R. D. Wilkes and M. J. Witty, Org. Prep. Proced. Int., 1994, 26, 702; (e) P. C. B. Page, M. T. Gareh and R. A. Porter, Tetrahedron: Asymmetry, 1993, 4, 2139.
2. V. K. Aggarwal, G. Evans, E. Moya and J. Dowden, J. Org. Chem., 1992, 57, 6390.
3. (a) Y. Watanabe, Y. Ono, S. Hayashi, Y. Ueno and T. Toru, J. Chem. Soc., Perkin Trans. 1, 1996, 1879; (b) Y. Watanabe, Y. Ono, Y. Ueno and T. Toru, J. Chem. Soc., Perkin Trans. 1, 1998, 1087.
4. (a) V. K. Aggarwal, R. Franklin, J. Maddock, G. R. Evans, A. Thomas, M. F. Mahon, K. C. Molloy and M. J. Rice, J. Org. Chem., 1995, 60, 2174; (b) V. K. Aggarwal, A. Thomas and S. Schade, Tetrahedron, 1997, 53, 16 213.
5. (a) P. K. Claus and F. W. Vierhapper, J. Chem. Soc., Chem. Commun., 1976, 1002; (b) R. B. Greenwald, D. H. Evans and J. R. DeMember, Tetrahedron Lett., 1975, 3885; (c) W. Errington, T. J. Sparey and P. C. Taylor, J. Chem. Soc., Perkin Trans. 2, 1994, 1439; (d) G. Smith, T. J. Sparey and P. C. Taylor, J. Chem. Soc., Perkin Trans. 1, 1996, 313.
6. (a) H. Takada, Y. Nishibayashi, K. Ohe and S. Uemura, Chem. Commun., 1996, 931; (b) H. Takada, Y. Nishibayashi, K. Ohe, S. Uemura, C. P. Baird, T. J. Sparey and P. C. Taylor, J. Org. Chem., 1997, 62, 6512.
7. Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889.
8. Attempts for sulfimidation of bis(phenylthio)methane, an acyclic dithioacetal, under the present conditions resulted in the formation of small amounts of seven unidentified products.
9. (a) D. Seebach, Synthesis, 1969, 1, 17; (b) B. F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti and A. Ricci, Tetrahedron, 1996, 52, 4803.
10. E. L. Eliel and R. O. Hutchins, J. Am. Chem. Soc., 1969, 91, 2703.
11. E. Juaristi, G. Cuevas and A. Vela, J. Am. Chem. Soc., 1994, 116, 5796.
12. Y. Yamada, T. Yamamoto and M. Okawara, Chem. Lett., 1975, 361.
13. H. Yoshida, T. Ogata and S. Inokawa, Synthesis, 1976, 552.