Copper-Catalyzed Asymmetric
Oxidation of Sulfides
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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)