Gallium trihalide catalyzed sequential addition of two different carbon nucleophiles to esters by using silyl cyanide and ketene silyl acetals

Abstract

A sequential addition of silyl cyanide and ketene silyl acetals to esters was achieved by a gallium trihalide catalyst to produce β-cyano-β-siloxy esters. This is the first example of the sequential addition of two different carbon nucleophiles to esters. The employment of lactones provided α,α-disubstituted cyclic ethers with a cyano group and an ester moiety. A variety of esters and lactones are applicable to this reaction system.

Keywords: esters; gallium; lactones; silicon; synthetic methods.