Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines

Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using (13)C-labelling and led to a revised mecha...

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Detalles Bibliográficos
Autores principales: Davies, Paul W, Martin, Nicolas, Spencer, Neil
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135223/
https://www.ncbi.nlm.nih.gov/pubmed/21804880
http://dx.doi.org/10.3762/bjoc.7.96
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author Davies, Paul W
Martin, Nicolas
Spencer, Neil
author_facet Davies, Paul W
Martin, Nicolas
Spencer, Neil
author_sort Davies, Paul W
collection PubMed
description Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using (13)C-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against the reaction of a range of (13)C- and deuterium-labelled substrates.
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spelling pubmed-31352232011-07-29 Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines Davies, Paul W Martin, Nicolas Spencer, Neil Beilstein J Org Chem Full Research Paper Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using (13)C-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against the reaction of a range of (13)C- and deuterium-labelled substrates. Beilstein-Institut 2011-06-21 /pmc/articles/PMC3135223/ /pubmed/21804880 http://dx.doi.org/10.3762/bjoc.7.96 Text en Copyright © 2011, Davies et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Davies, Paul W
Martin, Nicolas
Spencer, Neil
Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
title Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
title_full Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
title_fullStr Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
title_full_unstemmed Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
title_short Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
title_sort isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135223/
https://www.ncbi.nlm.nih.gov/pubmed/21804880
http://dx.doi.org/10.3762/bjoc.7.96
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AT spencerneil isotopiclabellingstudiesforagoldcatalysedskeletalrearrangementofalkynylaziridines

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