Copper-catalyzed asymmetric oxidation of sulfides |
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Authors: | O'Mahony Graham E Ford Alan Maguire Anita R |
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Affiliation: | Department of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland. |
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Abstract: | 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). |
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