Copper-catalyzed asymmetric oxidation of sulfides

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O'Mahony, Graham E.
Ford, Alan
Maguire, Anita R.
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Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee).
Copper-catalyzed , Asymmetric , Oxidation , Sulfides , Sulfoxidation
O’MAHONY, G. E., FORD, A. & MAGUIRE, A. R. 2012. Copper-Catalyzed Asymmetric Oxidation of Sulfides. Journal of organic chemistry, 77 (7), 3288-3296. doi: 10.1021/jo2026178
© 2011, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher.To access the final edited and published work see