Enantioselective preparation of 1,3-dithiane 1-oxides by asymmetric oxidation of 1,3-dithianes bearing a chiral auxiliary

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 15, 1996, Pages 1879-1885

  Watanabe, Yoshihiko ^a   Ono, Yojiro ^a   Hayashi, Shigefumi ^a   Ueno, Yoshio ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749087219     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001879     Document Type: Article

References (50)

1. J. A. Walker, Tetrahedron: Asymmetry, 1992, 3, 961;
2. H. B. Kagan and F. Rebiere, Synlett, 1990, 643.
3. P. C. B. Page, S. M. Allin, E. W. Collington and R. A. E. Carr, J. Org. Chem., 1993, 58, 6902;
4. P. C. B. Page, J. C. Prodger and D. Westwood, Tetrahedron, 1993, 49, 10355;
5. P. C. B. Page, M. T. Gareh and R. A. Porter, Tetrahedron Lett., 1993, 34, 5159;
6. P. C. B. Page, S. J. Shuttleworth, M. B. Schilling and D. J. Tapolczay, Tetrahedron Lett., 1993, 34, 6947;
7. P. C. B. Page and J. C. Prodger, Synlett., 1991, 84;
8. P. C. B. Page and J. C. Prodger, Synlett., 1990, 460;
9. P. C. B. Page, J. C. Prodger, M. Hursthouse and M. Mazid, J. Chem. Soc., Perkin Trans. 1, 1990, 167, 6947;
10. P. C. B. Page, D. Westwood and D. J. Slawin, J. Chem. Soc., Perkin Trans. 1, 1989, 185;
11. P. C. B. Page, S. S. Klair and D. Westwood, J. Chem. Soc., Perkin Trans. 1, 1989, 2441;
12. P. C. B. Page, D. Westwood, A. M. Z. Slawin and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1989, 1158.
13. K. K. Andersen, Tetrahedron Lett., 1962, 93;
14. K. K. Andersen, W. Gaffield, N. E. Papanikolaou, J. W. Foley and R. I. Perkins, J. Am. Chem. Soc., 1964, 88, 5637.
15. S. C. Benson and J. K. Snayder, Tetrahedron Lett., 1991, 32, 5885,
16. F. Wudl and T. B. K. Lee, J. Am. Chem. Soc., 1973, 95, 6349.
17. F. Rebiere, O. Samuel, L. Richard and K. B. Kagan, J. Org. Chem., 1991, 56, 5991.
18. P. Pitchen, E. Dunach, M. M. Deshmukh and H. B. Kagan, J. Am. Chem. Soc., 1984, 106, 8188;
19. P. Pitchen and H. B. Kagan, Tetrahedron Lett., 1984, 25, 1049.
20. F. D. Furia, G. Modena and R. Seraglia, Synthesis, 1984, 325;
21. F. A. Davis, R. H. Jenkins Jr., S. M. Awad, D. D. Stringer, W. H. Watson and J. Galloy, J. Am. Chem. Soc., 1982, 104, 5412.
22. Asymmetric oxidation using metalloporphyrins: L.-c. Chiang, K. Konishi, T. Aida and S. Inoue, J. Chem. Soc., Chem. Commun., 1992, 254;
23. Y. Naruta, F. Tani and K. Maruyama, Tetrahedron: Asymmetry, 1991, 2, 533;
24. R. L. Halterman, S. T. Jan and H. C. Nimmons, Synlett, 1991, 791;
25. T. T. Groves and P. Viski, J. Org. Chem., 1990, 55, 3628;
26. Y. Naruta, F. Tani and K. Maruyama, J. Chem. Soc., Chem. Commun., 1990, 1378;
27. Asymmetric oxidation using salen-Mn complexes. K. Imagawa, T. Nagata, T. Yamada and T. Mukaiyama, Chem. Lett., 1995, 335;
28. K. Noda, N. Hosoya, R. Irie, Y. Yamashita and T. Katsuki, Tetrahedron, 1994, 32, 9609;
29. K. Noda, N. Hosoya, K. Yanai, R. Irie and T. Katsuki, Tetrahedron Lett., 1994, 35, 1887;
30. M. Palucki, P. Hanson and E. N. Jacobsen, Tetrahedron Lett., 1992, 33, 7111.
31. P. C. B. Page, M. J. McKenzie and D. R. Buckle, J. Chem. Soc. Perkin Trans. 1, 1995, 2673;
32. F. A. Davis, R. T. Reddy, W. Han and P. J. Carroll, J. Am. Chem. Soc., 1992, 114, 1428;
33. P. C. B. Page and E. S. Namwindwa, Synlett., 1991, 80;
34. P. C. B. Page, E. S. Namwindwa, S. S. Klair and D. Westwood, Synlett, 1990, 457;
35. O. Samuel, B. Ronan and H. B. Kagan, J. Organomet. Chem., 1989, 370, 43.
36. P. C. B. Page, J. H. D. Bethell, E. W. Collington and D. M. Andrews, Synlett., 1995, 773;
37. V. K. Aggarwal, G. Evans, E. Moya and J. Dowden, J. Org. Chem., 1992, 57, 6390.
38. R. F. Bryan, F. A. Carey, Jr. O. D. Dailey, R. J. Maher and R. W. Miller, J. Org. Chem., 1978, 43, 90;
39. F. A. Carey, Jr., O. D. Dailey and W. C. Hutton, J. Org. Chem., 1978, 43, 96.
40. P. C. B. Page, R. D. Wilkes and M. J. Witty, Org. Prep. Proc. Intl., 1994, 26, 702;
41. P. C. B. Page, M. T. Gareh and R. A. Porter, Tetrahedron: Asymmetry, 1993, 4, 2139.
42. T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974.
43. S. D. Gero, D. Horton, A. M. Sepulchre and J. D. Wander, Tetrahedron, 1973, 29, 2963;
44. O. Theander, Acta. Chem. Scand., 1964, 18, 2209;
45. E. Brimacombe, J. S. Brimacombe and B. Lindberg, Acta. Chem. Scand., 1960, 14, 2236.
46. V. Conte, F. D. Furia, G. Licini and G. Modena, Tetrahedron Lett., 1989, 36, 4859.
47. R. M. Hanson and B. M. Sharpless, J. Org. Chem., 1986, 51, 1922.
48. N. P. C. Walker and D. Stuart, Acta Crystallogr., Sect. A, 1983, 39, 158.
49. J. A. Ibers and W. C. Hamilton, International Tables for X-Ray Crystallography, Kynoch, Birmingham, 1974, vol. IV.
50. B. A. Frenz, Enraf-Nonius Structure Determination Package; SDP User's Guide, Version 4, Enraf-Nonius, Delft, The Netherlands.