Unprecedented route to enolates from silyl enol ethers and enol acetates: reaction with hard and soft electrophiles

Abstract

Reaction of silyl enol ethers with lithium, sodium or, better, potassium alkoxides resulted in a rapid formation of enolates which were trapped with hard electrophiles and benzaldehyde. Moreover, in the aldolisation reaction, only a catalytic amount of alkali alkoxide is needed. This methodology is also applied to enol acetate. During these reactions a non-basic species, ether or ester, is produced with the enolate.