Stereoselective Synthesis of 1,3-Diol Derivatives Having Contiguous Stereogenic Centers from Acylsilanes

摘要

The treatment of acylsilanes having an enolizable methylene proton with LDA,followed by reaction of the resulting enolates 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.On the other hand,3-methoxyacylsilanes derived from the Mukaiyama-aldol reaction of acylsilane silyl enol ethers with aldehyde dimethyl acetals were treated with organometallic reagents to afford the corresponding 1,3-diol derivatives having the three contiguous Stereogenic centers in high yields with excellent diastereoselectivity.