Diastereoselective oxidation of 2,3-epoxy alcohol-derived thiiranes, and 1H NMR analysis of the corresponding thiirane s-oxides

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 126, Issue , 1997, Pages 223-234

  Carlier, Paul R ^a   Liu, Guilan ^a   Lam, H Y Peter ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031331383     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509708043562     Document Type: Article

References (16)

1. D. C. Dittmer, G. C. Levy, J. Org. Chem. 30, 636-638 (1965).
2. U. Zoller, in Syntheses of Sulphones, Sulphoxides, and Cyclic Sulphides S. Patai, Z. Rappoport, Eds. (John Wiley & Sons, New York, 1994) pp. 389-527.
3. M. D. Refvik, et al., J. Am. Chem. Soc. 117, 184-192 (1995).
4. F. Wu, X. Chen, B. R. Weiner, J. Am. Chem. Soc. 118, 8417-8424 (1996).
5. K. Kondo, A. Negishi, Tetrahedron 27, 4821-4830 (1971).
6. J. E. Baldwin, G. Höfle, S. C. Choi, J. Am. Chem. Soc. 93, 2810-2812 (1971).
7. J. R. Hurst, S. L. Wilson, G. B. Schuster, Tetrahedron 41, 2191-2197 (1985).
8. P. D. Bartlett, Rec. Chem. Prog. 18, 111(1957).
9. J. Brånalt, I. Kvarnström, S. C. T. Svensson, B. Classon, B. Samuelsson, J. Org. Chem. 59, 4430-4432 (1994).
10. As reported (Y. Gao, K. B. Sharpless J. Org. Chem. 53, 4114 (1988)), the Sharpless method developed for conversion of trans-2,3-epoxy alcohols to the corresponding thiirane derivatives does not work well for cis-2,3-epoxy alcohols such as 1a.
11. M. R. Binns, R. J. Goodridge, R. K. Haynes, D. D. Ridley, Tetrahedron Lett. 26, 6381-6384 (1985).
12. C. A. Kingsbury, J. Org. Chem. 37, 102-106 (1972).
13. E. Pretsch, J. Seibl, W. Simon, T. Clerc, in Spectral Data for Structure Determination of Organic Compounds(Springer-Verlag, New York, 1989) pp. H65-H100.
14. H. Friebolin, in Basic One-and Two-Dimensional NMR Spectroscopy(VCH Publishers, New York, 1993) pp. 87.
15. M. Ohtsuru, K. Tori, M. Fukuyama, Tetrahedron Lett. 33, 2877-2879 (1970).
16. We gratefully acknowledge financial support for this work from grants UGC/HKUST RI93/94.SCO1 and DAG96/97.SC12.