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Photocatalytic decarboxylative reduction of carboxylic acids and its application in asymmetric synthesis

Journal article
Authors Carlo Cassani
Giulia Bergonzini
Carl Johan Wallentin
Published in Organic Letters
Volume 16
Issue 16
Pages 4228-4231
ISSN 1523-7060
Publisher American Chemical Society
Publication year 2014
Published at Department of Chemistry and Molecular Biology
Pages 4228-4231
Language en
Links dx.doi.org/10.1021/ol5019294
Subject categories Chemical Sciences, Organic synthesis

Abstract

The decarboxylative reduction of naturally abundant carboxylic acids such as α-amino acids and α-hydroxy acids has been achieved via visible-light photoredox catalysis. By using an organocatalytic photoredox system, this method offers a mild and rapid entry to a variety of high-value compounds including medicinally relevant scaffolds. Regioselective decarboxylation is achieved when differently substituted dicarboxylic acids are employed. The application of this method to the synthesis of enantioenriched 1-aryl-2,2,2-trifluoroethyl chiral amines starting from natural α-amino acids further testifies to the utility of the developed photocatalytic decarboxylative reduction protocol.

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