Preparation of optically active α-Silylcarbonyl compounds using asymmetric alkylation of α-Silylacetic esters and asymmetric metal-carbene insertion into the Si-H bond.

Article abstract of DOI:10.1016/S0040-4020(97)00002-1

Substituted α-silylacetic esters have been prepared in good yields and with reasonable diastereoselectivities by three different routes. The first two involved alkylation of the parent α-silylacetic ester enolates, with the chiral auxiliaries being present either on silicon or on the ester function. The third route involving asymmetric insertion of metal-carbenoids into the Si-H band was found to afford better diastereoselectivities, using pantolactane as chiral auxiliary.