title: Asymmetric reduction of alpha-(trimethylsilyl)methyl-beta-ketosulfoxide with DIBAL under basic conditions.
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.
authors.affiliation: Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
authors.forename: Jun-Ichi
authors.initials: J
authors.lastname: Nakayama
authors.forename: Takeshi
authors.initials: T
authors.lastname: Toru