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Issue 2, 2012
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N-heterocyclic carbene cascade catalysis: Dual Brønsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones

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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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Supplementary files

Article information


Submitted
13 Sep 2011
Accepted
23 Sep 2011
First published
28 Sep 2011

Chem. Sci., 2012,3, 380-383
Article type
Edge Article

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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