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An efficient asymmetric oxidation of sulfides to sulfoxides
Authors:Philippe Pitchen  Henri B Kagan
Institution:Laboratoire de Synthése Asymétrique (Associé au CNRS, LA no 255) Université Paris-Sud, 91405 Orsay France
Abstract:The Sharpless reagent (Ti(OiPr)4 + 1 mol eq. diethyl tartrate (DET) + 2 t-BuOOH) modified by addition of one mol eq. H2O gives a new homogeneous reagent which cleanly oxidizes sulfides into sulfoxides in dichloromethane. The best results were obtained for the stoichiometry Ti/DET/H2O/t-BuOOH = 1:2:1:2. The e.e. observed ranged from 4 to 93% with the highest beeing observed in the case of methyl p-toly] sulfoxide.
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