Synthesis 2003(18): 2805-2810  
DOI: 10.1055/s-2003-42457
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Syntheses of (-)-(R)-Rolipram, (-)-(R)-Baclofen and Other GABA Analogues via Rhodium-Catalyzed Conjugate Addition of Arylboronic Acids

Jean-Michel Becht, Oliver Meyer, Günter Helmchen*
Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Fax: +49(6221)544205 ; e-Mail: g.helmchen@urz.uni-heidelberg.de;
Further Information

Publication History

Received 20 August 2003
Publication Date:
04 November 2003 (online)

Abstract

Highly enantioselective syntheses of two important γ-aminobutyric acid (GABA) analogues, the antispastic drug (-)-(R)-Baclofen and the antidepressant agent (-)-(R)-Rolipram, are reported. Key-steps in both syntheses are the Rh-catalyzed asymmetric 1,4-additions of arylboronic acids to 4-aminobut-2,3-enoic acid derivatives.