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Synthesis 2009(15): 2627-2633  
DOI: 10.1055/s-0029-1217405
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Hydrogenation of β-N-Substituted and β-N,N-Disubstituted Enamino Esters in the Presence of Iridium(I) Catalyst

Hania Hebbachea,b, Zakia Hanka, Christian Bruneau*b, Jean-Luc Renaud*c
a Laboratoire d’Électrochimie-Corrosion, Métallurgie et Chimie Minérale, Université des Sciences et Technologies Houari Boumedienne, Faculté de Chimie, BP32 El Alia 16111 Bab-Ezzouar, Alger, Algérie
b UMR 6226, CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Catalyse et Organométalliques, Campus de Beaulieu, 35042 Rennes Cedex, France
Fax: +33(2)23236939; e-Mail: christian.bruneau@univ-rennes1.fr;
c Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507, INC3M, FR 3038, ENSICAEN-Université de Caen, 14050 Caen, France
Fax: 33(2)31452877; e-Mail: jean-luc.renaud@ensicaen.fr;
Further Information

Publication History

Received 3 April 2009
Publication Date:
22 June 2009 (online)

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Abstract

Several new β-amino esters were prepared in two simple steps from β-keto ester derivatives and primary and secondary amines under mild conditions. The hydrogenation of various enamino esters was performed at 50 ˚C in the presence of iridium catalysts. The new β-N-substituted amino esters were isolated in high yields.

Key words

catalysis - hydrogenation - iridium - β-amino esters

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It was reported that trifluoroethanol was the best solvent for the hydrogenation of enamino esters and β-N-arylenamino esters in the presence of rhodium catalysts; see references 15 and 16.