Issue 2, 2012
From the journal:

Chemical Science

N-heterocyclic carbene cascade catalysis: Dual Brønsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones†

Lisa Candisha  and  David W. Lupton*a  

* Corresponding authors

a School of Chemistry, Monash University, Clayton, Australia
E-mail: david.lupton@monash.edu.
Fax: +613 9905 4597
Tel: +613 9902 0327

Abstract

The first example of Brønsted/Lewis base cascade catalysis using an N-heterocyclic carbene has been realised through the rearrangement of cyclopropyl esters to dihydropyranones. The scope and mechanism of this transformation has been examined implicating a novel NHC-mediated electrocyclic cyclopropane rearrangement followed by an anionic oxy Claisen-rearrangement.

Graphical abstract: N-heterocyclic carbene cascade catalysis: Dual Brønsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones

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Article information

DOI
https://doi.org/10.1039/C1SC00666E
Article type
Edge Article
Submitted
13 Sep 2011
Accepted
23 Sep 2011
First published
28 Sep 2011

Chem. Sci., 2012,3, 380-383

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N-heterocyclic carbene cascade catalysis: Dual Brønsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones

L. Candish and D. W. Lupton, Chem. Sci., 2012, 3, 380 DOI: 10.1039/C1SC00666E

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