Asymmetric reduction of α-(trimethylsilyl)methyl-β-ketosulfoxide with DIBAL under basic conditions

Article abstract of DOI:10.1021/jo034285k

The reaction of the α-carbanion of p-tolyl 2-(trimethylsilyl)ethyl sulfoxide with esters followed by reduction with DIBAL gave α-(trimethylsilyl)methyl-β-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.