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.