Direct palladium-catalyzed allylic alkylations of alcohols with enamines: Synthesis of homoallyl ketones

Abstract An efficient, direct nucleophilic allylic substitution of α-, β- and γ-substituted alcohols with enamines, using the Pd(OAc) 2/ PPh 3 catalyst system and ZnBr 2 as a promoter in CH 2 Cl 2 at reflux, is reported. The reaction course was dependent on the steric hindrance at the α- or γ-positions with respect to the functionalized α-carbon, selectively affording in moderate to good yields, α- or γ-homoallyl ketones, the so-called “linear” and “branched” products, respectively.