Issue 32, 2008

Enantioselective organocatalytic Michael additions to acrylic acid derivatives: generation of all-carbon quaternary stereocentres

Abstract

Acrylic esters, thioesters and N-acryloyl pyrrole have been identified as effective electrophiles in the enantioselective Michael addition reaction with β-keto ester pro-nucleophiles catalysed by a cinchona alkaloid derived bifunctional organocatalyst; enantiomeric excesses of up to 98% and yields of up to 96% can be obtained for a range of Michael acceptors and pro-nucleophiles.

Graphical abstract: Enantioselective organocatalytic Michael additions to acrylic acid derivatives: generation of all-carbon quaternary stereocentres

Supplementary files

Article information

Article type
Communication
Submitted
27 Mar 2008
Accepted
14 May 2008
First published
25 Jun 2008

Chem. Commun., 2008, 3798-3800

Enantioselective organocatalytic Michael additions to acrylic acid derivatives: generation of all-carbon quaternary stereocentres

C. L. Rigby and D. J. Dixon, Chem. Commun., 2008, 3798 DOI: 10.1039/B805233F

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