Highly diastereoselective oxidation of 1-alkylsulfinyl-9-(alkylthio)dibenzothiophene with mcpba in the presence of trifluoroboran etherate

Heterocycles

Volumn 42, Issue 1, 1996, Pages 71-74

  Kimura, Takeshi ^a   Nakayama, Hidetaka ^a   Furukawa, Naomichi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742539002     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s23     Document Type: Article

References (17)

1. For reviews, see: A. J. Walker, Tetrahedron Asymmetry, 1992, 3, 961; J. Drabowicz, P. Kielbasinski, and M. Mikolajczyk, The Chemistry of Sulfones and Sulfoxides', ed by S. Patai, Z. Rappoport, and C. Stirling, John Wiley & Sons, New York, 1988, pp. 233-378; M. Madesclaire, Tetrahedron, 1986, 42, 5459.
2. For reviews, see: A. J. Walker, Tetrahedron Asymmetry, 1992, 3, 961; J. Drabowicz, P. Kielbasinski, and M. Mikolajczyk, The Chemistry of Sulfones and Sulfoxides', ed by S. Patai, Z. Rappoport, and C. Stirling, John Wiley & Sons, New York, 1988, pp. 233-378; M. Madesclaire, Tetrahedron, 1986, 42, 5459.
3. For reviews, see: A. J. Walker, Tetrahedron Asymmetry, 1992, 3, 961; J. Drabowicz, P. Kielbasinski, and M. Mikolajczyk, The Chemistry of Sulfones and Sulfoxides', ed by S. Patai, Z. Rappoport, and C. Stirling, John Wiley & Sons, New York, 1988, pp. 233-378; M. Madesclaire, Tetrahedron, 1986, 42, 5459.
4. T. Shibutani, H. Fujihara, and N. Furukawa, Tetrahedron Lett., 1991, 32, 2947.
5. T. Kimura, H. Nakayama, and N. Furukawa, Chem. Lett., 1994, 27.
6. R. S. Glass, W. N. Setzer, U. D. G. Prabhu, and G. S. Wilson, Tetrahedron Lett., 1982, 23, 2335; R. S. Glass, A. Petsom, and G. S. Wilson, J. Org. Chem., 1987, 52, 3537.
7. R. S. Glass, W. N. Setzer, U. D. G. Prabhu, and G. S. Wilson, Tetrahedron Lett., 1982, 23, 2335; R. S. Glass, A. Petsom, and G. S. Wilson, J. Org. Chem., 1987, 52, 3537.
8. O. De Lucchi, V. Lucchini, C. Marchioro, G. Valle, and G. Modena, J. Org. Chem., 1986, 51, 1457.
9. N. Kunieda, J. Nokami, and M. Kinoshita, Chem. Lett., 1973, 871; N. Kunieda, J. Nokami, and M. Kinoshita, Bull. Chem. Soc. Jpn., 1976, 49, 256.
10. N. Kunieda, J. Nokami, and M. Kinoshita, Chem. Lett., 1973, 871; N. Kunieda, J. Nokami, and M. Kinoshita, Bull. Chem. Soc. Jpn., 1976, 49, 256.
11. 8
12. W. C. Hamilton, Acta Crystallogr., 1965, 18, 502; W. C. Hamilton, 'International Tables for X-Ray Crystallography, Vol IV'; ed by J. A. Ibers and W. C. Hamilton, Kynoch Press, Birmingham, 1973, pp. 285-310.
13. W. C. Hamilton, Acta Crystallogr., 1965, 18, 502; W. C. Hamilton, 'International Tables for X-Ray Crystallography, Vol IV'; ed by J. A. Ibers and W. C. Hamilton, Kynoch Press, Birmingham, 1973, pp. 285-310.
14. w=0.04271); the R values of the enantiomeric structure of 2a: R=0.04790 (Rw=0.05099).
15. 3), 7.58 (t, J=8.1 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.82 (t, J=8.1 Hz, 1H), 7.91 (d, J=8.1 Hz, 1H), 8.15 (d, J=8.1 Hz, 1H), 8.36 (d, J-8.1 Hz, 1H).
16. 3: C, 47.06; H, 4.19. Found: C, 46.86; H, 4.19.
17. N. Furukawa, T. Kimura, Y. Horie, S. Ogawa, and H. Fujihara, Tetrahedron Lett., 1992, 33, 1489.