A metal-catalyzed new approach for α-alkynylation of cyclic amines

The first catalytic α-alkynylation of cyclic amines with the help of the N-propargylic group to afford 2-(1-alkynyl) N-allylic cyclic amines with an exclusive E-stereoselectivity for the in situ formed C[double bond, length as m-dash]C bond has been realized. Based on mechanistic studies, it is prov...

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Detalles Bibliográficos
Autores principales: Cui, Yifan, Lin, Weilong, Ma, Shengming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6369436/
https://www.ncbi.nlm.nih.gov/pubmed/30842847
http://dx.doi.org/10.1039/c8sc04115f
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author Cui, Yifan
Lin, Weilong
Ma, Shengming
author_facet Cui, Yifan
Lin, Weilong
Ma, Shengming
author_sort Cui, Yifan
collection PubMed
description The first catalytic α-alkynylation of cyclic amines with the help of the N-propargylic group to afford 2-(1-alkynyl) N-allylic cyclic amines with an exclusive E-stereoselectivity for the in situ formed C[double bond, length as m-dash]C bond has been realized. Based on mechanistic studies, it is proven that the reaction proceeds through metal-mediated anti-1,5-hydride transfer forming an iminonium intermediate, which accepts the addition of the in situ generated 1-alkynyl metal species. The synthetic application has also been demonstrated.
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spelling pubmed-63694362019-03-06 A metal-catalyzed new approach for α-alkynylation of cyclic amines Cui, Yifan Lin, Weilong Ma, Shengming Chem Sci Chemistry The first catalytic α-alkynylation of cyclic amines with the help of the N-propargylic group to afford 2-(1-alkynyl) N-allylic cyclic amines with an exclusive E-stereoselectivity for the in situ formed C[double bond, length as m-dash]C bond has been realized. Based on mechanistic studies, it is proven that the reaction proceeds through metal-mediated anti-1,5-hydride transfer forming an iminonium intermediate, which accepts the addition of the in situ generated 1-alkynyl metal species. The synthetic application has also been demonstrated. Royal Society of Chemistry 2018-11-26 /pmc/articles/PMC6369436/ /pubmed/30842847 http://dx.doi.org/10.1039/c8sc04115f Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Cui, Yifan
Lin, Weilong
Ma, Shengming
A metal-catalyzed new approach for α-alkynylation of cyclic amines
title A metal-catalyzed new approach for α-alkynylation of cyclic amines
title_full A metal-catalyzed new approach for α-alkynylation of cyclic amines
title_fullStr A metal-catalyzed new approach for α-alkynylation of cyclic amines
title_full_unstemmed A metal-catalyzed new approach for α-alkynylation of cyclic amines
title_short A metal-catalyzed new approach for α-alkynylation of cyclic amines
title_sort metal-catalyzed new approach for α-alkynylation of cyclic amines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6369436/
https://www.ncbi.nlm.nih.gov/pubmed/30842847
http://dx.doi.org/10.1039/c8sc04115f
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AT mashengming ametalcatalyzednewapproachforaalkynylationofcyclicamines
AT cuiyifan metalcatalyzednewapproachforaalkynylationofcyclicamines
AT linweilong metalcatalyzednewapproachforaalkynylationofcyclicamines
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