1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides

Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C–N bond cleavage of the yn...

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Detalles Bibliográficos
Autores principales: Adcock, Holly V, Langer, Thomas, Davies, Paul W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4204129/
https://www.ncbi.nlm.nih.gov/pubmed/24828030
http://dx.doi.org/10.1002/chem.201403040
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author Adcock, Holly V
Langer, Thomas
Davies, Paul W
author_facet Adcock, Holly V
Langer, Thomas
Davies, Paul W
author_sort Adcock, Holly V
collection PubMed
description Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C–N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity.
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spelling pubmed-42041292014-11-12 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides Adcock, Holly V Langer, Thomas Davies, Paul W Chemistry Communications Unique α-hemiaminal ether gold carbene intermediates were accessed by a gold-catalysed 1,1-carboalkoxylation strategy and evolved through a highly selective 1,2-N-migration. This skeletal rearrangement gave functionalised indenes, and isotopic labelling confirmed the rare C–N bond cleavage of the ynamide moiety. The effect of substituents on the migration has been explored, and a model is proposed to rationalise the observed selectivity. WILEY-VCH Verlag 2014-06-10 2014-05-14 /pmc/articles/PMC4204129/ /pubmed/24828030 http://dx.doi.org/10.1002/chem.201403040 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by-nc/3.0/ This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Adcock, Holly V
Langer, Thomas
Davies, Paul W
1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides
title 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides
title_full 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides
title_fullStr 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides
title_full_unstemmed 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides
title_short 1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides
title_sort 1,2-n-migration in a gold-catalysed synthesis of functionalised indenes by the 1,1-carboalkoxylation of ynamides
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4204129/
https://www.ncbi.nlm.nih.gov/pubmed/24828030
http://dx.doi.org/10.1002/chem.201403040
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AT daviespaulw 12nmigrationinagoldcatalysedsynthesisoffunctionalisedindenesbythe11carboalkoxylationofynamides

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