On the Palladium-Catalyzed Alkylation of Silyl-Substituted Allyl Acetates with Enolates

Article abstract of DOI:10.1021/jo00177a016

Treatment of lithium enolates with trialkylstannyl trifluoroacetates permits their use as nucleophiles in allylic alkylations catalyzed by palladium with high regioselectivity and without polyalkylation.Alkylation without concomitant desilylation occurs for 3-acetoxy-1-(trimethylsilyl)-1-propene and n-butyl 2-acetoxy-4-(trimethylsilyl)-3-butenoate under these conditions.The choice of substituents on the tin does affect the rate of the alkylation; trimethyl substitution proceeds substantially faster than tri-n-butyl substitution.