Issue 93, 2014
From the journal:

Chemical Communications

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

Santigopal Mondal,a   Santhivardhana Reddy Yetra,a   Atanu Patra,a   Sunita S. Kunte,a   Rajesh G. Gonnadeb  and  Akkattu T. Biju*a  

* Corresponding authors

a Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
E-mail: at.biju@ncl.res.in
Fax: +91-20-25902629
Tel: +91-20-25902441

b Centre for Materials Characterization, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India

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

DOI
https://doi.org/10.1039/C4CC07433E
Article type
Communication
Submitted
20 Sep 2014
Accepted
06 Oct 2014
First published
06 Oct 2014

Chem. Commun., 2014,50, 14539-14542

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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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