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

[Display omitted] •Direct catalytic allylic alkylation of enamines with alcohols.•Rapid conversion of α-,β- and γ-substituted alcohols into α-allyl ketones.•A highly regioselective protocol for the synthesis of α- or γ-homoallyl ketones.•A common palladium-based catalyst (Pd(OAc)2), a phosphine ligand (PPh3), and an inexpensive Lewis acid. An efficient, direct nucleophilic allylic substitution of α-, β- and γ-substituted alcohols with enamines, using the Pd(OAc)2/PPh3 catalyst system and ZnBr2 as a promoter in CH2Cl2 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.