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Asymmetric reduction of alpha-(trimethylsilyl)methyl-beta-ketosulfoxide with DIBAL under basic conditions
Shuichi Nakamura1, Jun-Ichi Nakayama, Takeshi Toru
1Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
The Journal of Organic Chemistry
|July 4, 2003
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.