Issue 4, 2015

N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

Abstract

N-Heterocyclic carbene catalysed redox isomerisation with reduction about the carbonyl has been developed in the transformation of trienyl esters to tetrasubstituted benzaldehydes. The reaction proceeds in good to excellent yield, and in cases that provide 2,2′-biaryls, enantioselectivity is observed. Mechanistic studies demonstrate the intermediacy of a cyclohexenyl β-lactone, while implicating formation of the homoenolate as turnover limiting.

Graphical abstract: N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Dec 2014
Accepted
22 Jan 2015
First published
26 Jan 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 2366-2370

Author version available

N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

L. Candish, A. Levens and D. W. Lupton, Chem. Sci., 2015, 6, 2366 DOI: 10.1039/C4SC03726J

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