Enantioselective Pummerer-type rearrangement by reaction of O-silylated ketene acetal with enantiopure α-substituted sulfoxides

Abstract

Chiral non-racemic α-substituted sulfoxides have been allowed to react with O-silylated ketene acetals in the presence of a catalytic amount of ZnI2 in THF to give chiral non-racemic α-siloxy sulfides in >99% ee. This is the highest enantioselectivity reported to date for the Pummerer reaction.