Diastereoselective conversion of sulfides into sulfoxides. 1,5- and 1,6-asymmetric induction

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1996, Pages 333-342

  Bower, Justin F ^a   Martin, Christopher J ^a   Rawson, David J ^b   Slawin, Alexandra M Z ^a   Williams, Jonathan M J ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542713020     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000333     Document Type: Article

References (32)

1. G. H. Posner, Asymmetric Synthesis, ed. D. Morrison and J. W. Scott, Academic Press, New York, 1983, vol. 2, p. 225.
2. G. Solladié and N. Huser, Tetrahedron Lett., 1994, 35, 5297.
3. N. Khiar, I. Fernández and F. Alcudia, Tetrahedron Lett., 1993, 34, 123;
4. M. C. Carreño and J. L. Garciá Ruano, J. Org. Chem., 1993, 58, 4529.
5. I. Alonso, J. C. Carretero and J. L. Garcia Ruano, J. Org. Chem., 1993, 58, 3231;
6. G. H. Posner and W. Harrison, J. Chem. Soc., Chem. Commun., 1985, 1786.
7. R. J. Butlin, I. D. Linney, D. J. Critcher, M. F. Mahon, K. C. Molloy and M. Wills, J. Chem. Soc., Perkin Trans. 1, 1993, 1581.
8. A. J. Walker, Tetrahedron: Asymmetry, 1992, 3, 961.
9. (a) M. Shimazaki, M. Takahashi, H. Komatsu, A. Ohta, K. Kajii and Y. Kodama, Synthesis, 1992, 555;
10. (b) R. Breitschuh and D. Seebach, Synthesis, 1992, 1170;
11. (c) G. Delogu, O. De Lucchi, M. Paola Fois and G. Valle, Phosphorus Sulfur Silicon Relat. Elem., 1990, 47, 417;
12. (d) T. Sato and J. Otera, Synlett, 1995, 365;
13. (e) G. O. Danelon, E. G. Mata and O. A. Mascaretti, Tetrahedron Lett., 1993, 34, 7877;
14. (f) R. Siedlecka and J. Skarzewski, Synthesis, 1994, 401;
15. (g) W. Adam and D. Golsch, Chem. Ber., 1994, 127, 1111.
16. T. G. Gant and A. I. Meyers, Tetrahedron, 1994, 50, 2297.
17. J. V. Allen, G. J. Dawson, C. G. Frost and J. M. J. Williams, Tetrahedron, 1994, 50, 799.
18. J. V. Allen, J. F. Bower and J. M. J. Williams, Tetrahedron: Asymmetry, 1994, 5, 1895;
19. J. F. Bower and J. M. J. Williams, Tetrahedron Lett., 1994, 35, 7111.
20. C. Bolm, K. Weickhardt, M. Zehnder and T. Ranff, Chem. Ber., 1991, 124, 1173.
21. D. P. Schumacker, J. E. Clark, B. L. Murphy and P. A. Fischer, J. Org. Chem., 1990, 55, 5291.
22. Y. Arai, M. Matsui, T. Koizumi and M. Shiro, J. Org. Chem., 1991, 56, 1983;
23. O. De Lucchi, V. Lucchini, C. Marchioro. G. Valle and G. Modena, J. Org. Chem., 1986, 51, 1457.
24. L. A. Carpino and H.-W. Chen, J. Am. Chem. Soc., 1979, 101, 390.
25. N. J. Leonard and C. R. Johnson, J. Org. Chem., 1962, 27, 282.
26. A. McKillop and J. A. Tarben, Tetrahedron Lett., 1983, 24, 1505.
27. P. Brougham, M. S. Cooper, D. A. Cummerson, H. Heaney and N. Thompson, Synthesis, 1987, 1015.
28. S. H. Zhao, O. Samuel and H. B. Kagan, Tetrahedron, 1987, 43, 5135.
29. K. K. Andersen, W. Gaffield, N. E. Papanikolaou, J. W. Foley and R. I. Perkins, J. Am. Chem. Soc., 1964, 86, 5637.
30. A. H. Hoveyda, D. A. Evans and G. C. Fu, Chem. Rev., 1993, 93, 1307.
31. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 1972, 94, 6190.
32. TEXSAN; Crystal Structure Analysis Package, Molecular Structure Corporation, 1985 and 1992.