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Rhodium-catalyzed asymmetric addition of arylboronic acids to γ-phthalimido-substituted-α,β-unsaturated carboxylic acid esters: an approach to γ-amino acids

✍ Scribed by Fuzhong Han; Jun Chen; Xiangyang Zhang; Jibing Liu; Linfeng Cun; Jin Zhu; Jingen Deng; Jian Liao

Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 412 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.12.044

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✦ Synopsis

Efficient Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to ethyl-c-phthalimidocrotonate by using bis-sulfoxide ligand affords c-aminobutyric acid (GABA) derivatives with high enantioselectivities (90-96% ee) under mild conditions. Optically pure (S)-Baclofen and (S)-Rolipram have been prepared successfully through this synthetic route.

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## Abstract Rhodium fluoroapatite (RhFAP) is an efficient catalyst for conjugate addition of organoboron reagents to __α__,__β__‐unsaturated carbonyl compounds. A variety of arylboronic acids and __α__,__β__‐unsaturated carbonyl compounds were converted to the corresponding conjugate‐addition produ