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

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 observe...

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Detalles Bibliográficos
Autores principales: Candish, Lisa, Levens, Alison, Lupton, David W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5645917/
https://www.ncbi.nlm.nih.gov/pubmed/29308150
http://dx.doi.org/10.1039/c4sc03726j
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author Candish, Lisa
Levens, Alison
Lupton, David W.
author_facet Candish, Lisa
Levens, Alison
Lupton, David W.
author_sort Candish, Lisa
collection PubMed
description 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.
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spelling pubmed-56459172018-01-05 N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes Candish, Lisa Levens, Alison Lupton, David W. Chem Sci Chemistry 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. Royal Society of Chemistry 2015-04-01 2015-01-26 /pmc/articles/PMC5645917/ /pubmed/29308150 http://dx.doi.org/10.1039/c4sc03726j Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Candish, Lisa
Levens, Alison
Lupton, David W.
N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
title N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
title_full N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
title_fullStr N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
title_full_unstemmed N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
title_short N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
title_sort n-heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5645917/
https://www.ncbi.nlm.nih.gov/pubmed/29308150
http://dx.doi.org/10.1039/c4sc03726j
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AT luptondavidw nheterocycliccarbenecatalysedredoxisomerisationofesterstofunctionalisedbenzaldehydes

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