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Issue 93, 2014
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N-Heterocyclic carbene-catalyzed enantioselective synthesis of functionalized cyclopentenes via α,β-unsaturated acyl azoliums

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Abstract

Highly enantioselective NHC-organocatalyzed synthesis of functionalized cyclopentenes proceeding via α,β-unsaturated acyl azolium intermediates is reported. The organocascade reaction of modified enals with malonic ester derivatives having a γ-benzoyl group involves the Michael–intramolecular aldol-β-lactonization–decarboxylation sequence to deliver cyclopentenes in good yields and excellent ee values.

Graphical abstract: N-Heterocyclic carbene-catalyzed enantioselective synthesis of functionalized cyclopentenes via α,β-unsaturated acyl azoliums

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Article information


Submitted
20 Sep 2014
Accepted
06 Oct 2014
First published
06 Oct 2014

Chem. Commun., 2014,50, 14539-14542
Article type
Communication
Author version available

N-Heterocyclic carbene-catalyzed enantioselective synthesis of functionalized cyclopentenes via α,β-unsaturated acyl azoliums

S. Mondal, S. R. Yetra, A. Patra, S. S. Kunte, R. G. Gonnade and A. T. Biju, Chem. Commun., 2014, 50, 14539
DOI: 10.1039/C4CC07433E

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