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A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides
Gold‐catalysed oxidative cyclisation reactions of ynamides offer great promise in γ‐lactam synthesis but are limited by preferential over‐oxidation to form α‐keto imides. Evaluating the factors that might limit N‐cyclisation pathways led to effective gold‐catalysed conditions that allow access to di...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6282577/ https://www.ncbi.nlm.nih.gov/pubmed/30248205 http://dx.doi.org/10.1002/chem.201804378 |
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author | Sánchez‐Cantalejo, Fernando Priest, Joshua D. Davies, Paul W. |
author_facet | Sánchez‐Cantalejo, Fernando Priest, Joshua D. Davies, Paul W. |
author_sort | Sánchez‐Cantalejo, Fernando |
collection | PubMed |
description | Gold‐catalysed oxidative cyclisation reactions of ynamides offer great promise in γ‐lactam synthesis but are limited by preferential over‐oxidation to form α‐keto imides. Evaluating the factors that might limit N‐cyclisation pathways led to effective gold‐catalysed conditions that allow access to different fused γ‐lactams on changing the ynamide N‐substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3‐aryl indoles and cyclohepta[c]pyrrol‐1‐one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals. |
format | Online Article Text |
id | pubmed-6282577 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-62825772018-12-11 A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides Sánchez‐Cantalejo, Fernando Priest, Joshua D. Davies, Paul W. Chemistry Communications Gold‐catalysed oxidative cyclisation reactions of ynamides offer great promise in γ‐lactam synthesis but are limited by preferential over‐oxidation to form α‐keto imides. Evaluating the factors that might limit N‐cyclisation pathways led to effective gold‐catalysed conditions that allow access to different fused γ‐lactams on changing the ynamide N‐substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3‐aryl indoles and cyclohepta[c]pyrrol‐1‐one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals. John Wiley and Sons Inc. 2018-10-30 2018-11-22 /pmc/articles/PMC6282577/ /pubmed/30248205 http://dx.doi.org/10.1002/chem.201804378 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Sánchez‐Cantalejo, Fernando Priest, Joshua D. Davies, Paul W. A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides |
title | A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides |
title_full | A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides |
title_fullStr | A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides |
title_full_unstemmed | A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides |
title_short | A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides |
title_sort | gold carbene manifold to prepare fused γ‐lactams by oxidative cyclisation of ynamides |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6282577/ https://www.ncbi.nlm.nih.gov/pubmed/30248205 http://dx.doi.org/10.1002/chem.201804378 |
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