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Synlett 1995; 1995(7): 773-775
DOI: 10.1055/s-1995-5061
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Highly Enantioselective Catalytic Asymmetric Oxidation of Sulfides using Hydrogen Peroxide

P. C. Bulman Page* , J. P. Heer, D. Bethell, E. W. Collington, D. M. Andrews
  • *Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Oxford Street, Liverpool L69 3BX, England, Fax +44 151 794 3522; pcbpage@liv.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Hydrogen peroxide in conjunction with enantiomerically pure sulfonylimines has been used for the catalytic enantioselective oxidation of a range of dialkyl sulfides under basic conditions in very high yields. The highest enantioselectivities (up to ca. 98%) were obtained using acetals of oxocamphorsulfonylimine as mediators. This process is inexpensive, environmentally friendly and remarkably simple, requiring minimum work up and no close monitoring. The reactive intermediate is currently formulated as an α-hydroperoxyamine.

Asymmetric - Enantioselective - Oxidation - Sulfoxide