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Issue 42, 2012

Enantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis

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Abstract

Carbene catalysed redox activation of α,β-unsaturated aldehydes is applied for generation of α,β-unsaturated acyl azoliums which undergo cyclopropanation upon reaction with a sulfur ylide and an alcohol to give the corresponding cyclopropanecarboxylic acid esters. With chiral carbenes good to excellent diastereo and enantioselectivities are obtained.

Graphical abstract: Enantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis

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Article information


Submitted
28 Feb 2012
Accepted
29 Mar 2012
First published
18 Apr 2012

Chem. Commun., 2012,48, 5190-5192
Article type
Communication

Enantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis

A. Biswas, S. De Sarkar, L. Tebben and A. Studer, Chem. Commun., 2012, 48, 5190 DOI: 10.1039/C2CC31501G

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