Selective catalytic hydrogenation of gamma-amino alfa,beta-unsaturated esters in the presence of hydrogenable protecting groups

The chemoselective catalytic hydrogenation of substituted γ-amino α,β-unsaturated esters bearing benzyl ether, benzyl ester functionalities and N-Cbz protecting groups by 3% Pd/C in EtOAc was investigated. The results revealed a good selectivity for substrates with benzyl ethers and benzyl esters in the side chain and for α,β-unsaturated benzyl esters. Moderate selectivity was observed for substrates with N-Cbz protecting group.