Palladium-catalyzed selective alkoxycarbonylation of α,β-unsaturated amides: a novel approach toward new ω-amido esters and N-substituted cyclic succinimides

The alkoxycarbonylation of alpha,beta-unsaturated amides proceeded efficiently and regioselectivity to give omega-amido esters with complete conversion in the presence of the catalyst system: Pd(PPh(3))(2)Cl(2)/MeOH/CO/H(2)O. The reaction was successfully applied to the alkoxycarbonylation of bis-acrylamides yielding, selectively, the corresponding di-omega-amido esters. These mono and di-omega-amido esters have been used as precursors for the synthesis of N-substituted cyclic succinimides in moderate to high yields. (C) 2010 Elsevier Ltd. All rights reserved.