Experimental study demonstrates highly enantioselective sulfoxidation in aryl alkyl sulfides using chiral zirconium(IV) catalysts, indicating an effective dual-step asymmetric pathway.
Partially-hydrolized chiral Zr(IV) catalysts, based on C3 symmetric trialkanolamine ligands 1a-c in the presence of cumyl hydroperoxide, provide a new homogeneous system for the enantioselective sulfoxidation of a wide range of aryl alkyl sulfides. Ee’s in the range 80-90% are obtained, through the cooperative effect of two independent stereoselective processes, namely the direct asymmetric oxidation of the sulfide to the sulfoxide and its subsequent kinetic resolution to sulfone, allowing the recover of the desired product with yields up to 35%. In every reaction the peroxide is converted quantitatively with as little as 2% of catalyst
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Bonchio et al. (1999) studied this question.
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