Stereoselective Tandem Aldol-Tishchenko Reaction with Acylsilanes

The treatment of acetyltrimethylsilane with LDA, followed by reaction of the resulting enolate with the excess amount of aldehydes gave the corresponding 1,3-diol derivatives in moderate yields with perfect diastereoselectivity as a single regioisomer via tandem aldol-Tishchenko reaction, whereas the reaction with α-branched aldehydes under similar conditions gives a mixture of two regioisomers. The reaction using benzyl trimethylsilyl ketone afforded the corresponding 1,3-diol monoesters having three contiguous stereogenic centers with perfect levels of stereochemical control in one-pot.