Selective Catalytic Hydrogenation of γ-Amino α,β-Unsaturated Esters in the Presence of Hydrogenable Protecting Groups

Domenico Misiti; Giovanni Zappia; Giuliano Delle Monache

doi:10.1055/s-1999-3471

Synthesis 1999; 1999(5): 873-877
DOI: 10.1055/s-1999-3471

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Selective Catalytic Hydrogenation of γ-Amino α,β-Unsaturated Esters in the Presence of Hydrogenable Protecting Groups

Domenico Misiti^* , Giovanni Zappia, Giuliano Delle Monache

^*Dip. di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università "La Sapienza", P.le A. Moro 5, 00185 Roma, Italy; Fax +39(6)49 91 27 80; E-mail: g.zappia@caspur.it

Abstract

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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.

chemoselective hydrogenation - 3% Pd/C - γ-amino α,β-unsaturated esters - protected γ-amino acids

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