Abstract
The reaction of the alpha-carbanion of p-tolyl 2-(trimethylsilyl)ethyl sulfoxide with esters followed by reduction with DIBAL gave alpha-(trimethylsilyl)methyl-beta-hydroxysulfoxides with high stereoselectivity. The stereoselective reaction was demonstrated to proceed through a dynamic kinetic resolution pathway via a six-membered cyclic transition state involving Si-O interaction. These reactions provide a convenient route for the synthesis of optically pure allylic alcohols.
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