Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Sánchez‐Cantalejo, Fernando, Priest, Joshua D., Davies, Paul W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
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
_version_ 1783379024497606656
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
work_keys_str_mv AT sanchezcantalejofernando agoldcarbenemanifoldtopreparefusedglactamsbyoxidativecyclisationofynamides
AT priestjoshuad agoldcarbenemanifoldtopreparefusedglactamsbyoxidativecyclisationofynamides
AT daviespaulw agoldcarbenemanifoldtopreparefusedglactamsbyoxidativecyclisationofynamides
AT sanchezcantalejofernando goldcarbenemanifoldtopreparefusedglactamsbyoxidativecyclisationofynamides
AT priestjoshuad goldcarbenemanifoldtopreparefusedglactamsbyoxidativecyclisationofynamides
AT daviespaulw goldcarbenemanifoldtopreparefusedglactamsbyoxidativecyclisationofynamides