Vanadium-catalyzed Enantioselective Sulfoxidation of Methyl Aryl Sulfides with Hydrogen Peroxide as Terminal Oxidant

Abstract

Chiral vanadium complex prepared in situ from VO(acac)₂ and Schiff base 9 was found to be an efficient catalyst for oxidation of various methyl aryl sulfides with hydrogen peroxide as terminal oxidant. For example, oxidation of methyl 2-naphthyl sulfide using a VO(acac)₂, 9, and hydrogen peroxide system proceeded with high enantioselectivity of 93% ee as well as acceptable chemical yield.

Key words

asymmetric catalysis - chiral vanadium complex - Schiff base - enantioselective sulfoxidation - hydrogen peroxide

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13

Although we synthesized compound 8 according to the reported procedure (ref. [14] ), it can be prepared enantioselectively in a short step by using Yamamoto procedure (ref. [15] ).