155394-03-9

Upstream product

• 78-84-2 isobutyraldehyde 
• 153123-09-2 (R_S)-p-Tolyl β-(trimethylsilyl)ethyl sulfoxide 
• 97-62-1 Ethyl isobutyrate 
• 1519-39-7 (R)-methyl p-tolyl sulfoxide 

Relevant academic research and scientific papers

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

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.

Vinyl Anion Equivalent V. Asymmetric Synthesis of Allylic Alcohols Using Chiral 2-(Trialkylsilyl)ethyl Sulfoxides

Both enantiomers of optically pure secondary allylic alcohols can be conveniently prepared by the diastereoselective reaction of the α-sulfinyl carbanion of p-tolyl 2-(trialkylsilyl)ethyl sulfoxides or tert-butyl 2-(trimethylsilyl)ethyl sulfoxide with aldehydes followed by either fluoride-induced desilylsulfinylation or thermal elimination of the sulfinyl group.