Issue 2, 2012

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
13 Sep 2011
Accepted
23 Sep 2011
First published
28 Sep 2011

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

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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