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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...
An efficient nucleophilic allylic substitution of a variety of Morita–Baylis–Hillman adducts with enamines catalyzed by Pd(OAc)2 in the presence of ZnBr2 as a promoter is described in the present study. The reaction gives SN2-type 1,5-dicarbonyl compounds that may subsequently undergo an intramolecular conjugate addition onto the enone moiety affording the corresponding 1,4-adducts. All the synthesized...
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