Three-component reaction to synthesize E-vinyl silyl anti-1,2-diols via sequential [1,4]-O-to-O/[1,4]-C-to-O silyl migrations

Abstract

A three-component reaction of geminal bis(silyl) allyl silyl ether, aldehyde and electrophile has been developed to synthesize trisubstituted E-vinyl silyl anti-1,2-diols. The approach features sequential [1,4]-O-to-O/[1,4]-C-to-O silyl migrations, which are triggered by the addition of the exo-oriented allyl anion to an aldehyde and terminated by the coupling of the resulting vinyl cuprate and electrophiles.