Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction

A novel class of chiral N,N,N imine-containing ligands derived from TsDPEN (N-(p-tosyl)-1,2-diphenylethylene-1,2-diamine) has been developed and applied to the copper-catalyzed asymmetric Kinugasa reaction. The copper(ii) salt proved to be an efficient catalyst precursor, and it provides an efficien...

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Autores principales: Xu, Chuanlong, Yang, Yuchen, Wu, Yue, He, Feilong, He, Huakang, Deng, Ping, Zhou, Hui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9053751/
https://www.ncbi.nlm.nih.gov/pubmed/35517194
http://dx.doi.org/10.1039/d0ra03276j
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author Xu, Chuanlong
Yang, Yuchen
Wu, Yue
He, Feilong
He, Huakang
Deng, Ping
Zhou, Hui
author_facet Xu, Chuanlong
Yang, Yuchen
Wu, Yue
He, Feilong
He, Huakang
Deng, Ping
Zhou, Hui
author_sort Xu, Chuanlong
collection PubMed
description A novel class of chiral N,N,N imine-containing ligands derived from TsDPEN (N-(p-tosyl)-1,2-diphenylethylene-1,2-diamine) has been developed and applied to the copper-catalyzed asymmetric Kinugasa reaction. The copper(ii) salt proved to be an efficient catalyst precursor, and it provides an efficient way to synthesize enantioenriched cis-β-lactam. The pathway is air-tolerant and easily manipulated, and the ligands are easy to synthesize. A working model is proposed in which the stereocontrolling step is the [2 + 2] cycloaddition between ketene and imine to explain the observed stereoselectivities.
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spelling pubmed-90537512022-05-04 Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction Xu, Chuanlong Yang, Yuchen Wu, Yue He, Feilong He, Huakang Deng, Ping Zhou, Hui RSC Adv Chemistry A novel class of chiral N,N,N imine-containing ligands derived from TsDPEN (N-(p-tosyl)-1,2-diphenylethylene-1,2-diamine) has been developed and applied to the copper-catalyzed asymmetric Kinugasa reaction. The copper(ii) salt proved to be an efficient catalyst precursor, and it provides an efficient way to synthesize enantioenriched cis-β-lactam. The pathway is air-tolerant and easily manipulated, and the ligands are easy to synthesize. A working model is proposed in which the stereocontrolling step is the [2 + 2] cycloaddition between ketene and imine to explain the observed stereoselectivities. The Royal Society of Chemistry 2020-05-12 /pmc/articles/PMC9053751/ /pubmed/35517194 http://dx.doi.org/10.1039/d0ra03276j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Xu, Chuanlong
Yang, Yuchen
Wu, Yue
He, Feilong
He, Huakang
Deng, Ping
Zhou, Hui
Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction
title Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction
title_full Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction
title_fullStr Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction
title_full_unstemmed Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction
title_short Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction
title_sort development of tsdpen based imine-containing ligands for the copper-catalysed asymmetric kinugasa reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9053751/
https://www.ncbi.nlm.nih.gov/pubmed/35517194
http://dx.doi.org/10.1039/d0ra03276j
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