155394-01-7Relevant articles and documents
Asymmetric reduction of α-(trimethylsilyl)methyl-β-ketosulfoxide with DIBAL under basic conditions
Nakamura, Shuichi,Nakayama, Jun-ichi,Toru, Takeshi
, p. 5766 - 5768 (2007/10/03)
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.