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Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines

An Ir-catalyzed intramolecular asymmetric reductive amination (ARA) of bridged biaryl derivatives has been described. Using this unprecedented approach, synthetically useful dibenz[c,e]azepines containing both central and axial chiralities are obtained with excellent enantiocontrol (up to 97% ee). T...

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Detalles Bibliográficos
Autores principales: Yang, Tao, Guo, Xiaochong, Yin, Qin, Zhang, Xumu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385856/
https://www.ncbi.nlm.nih.gov/pubmed/30881676
http://dx.doi.org/10.1039/c8sc04482a
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author Yang, Tao
Guo, Xiaochong
Yin, Qin
Zhang, Xumu
author_facet Yang, Tao
Guo, Xiaochong
Yin, Qin
Zhang, Xumu
author_sort Yang, Tao
collection PubMed
description An Ir-catalyzed intramolecular asymmetric reductive amination (ARA) of bridged biaryl derivatives has been described. Using this unprecedented approach, synthetically useful dibenz[c,e]azepines containing both central and axial chiralities are obtained with excellent enantiocontrol (up to 97% ee). This methodology represents a rare example of enantioselective chemocatalytic synthesis of chiral dibenz[c,e]azepines featuring a broad substrate scope, and their synthetic utilities are exhibited by derivatizing the products into a chiral amino acid derivative and chiral phosphoramidite ligands, which display excellent enantiocontrol in Rh-catalyzed asymmetric hydrogenation of α-dehydroamino acid derivatives. Remarkably, our method is also applicable to enantioselectively synthesize an allocolchicine analogue.
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spelling pubmed-63858562019-03-15 Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines Yang, Tao Guo, Xiaochong Yin, Qin Zhang, Xumu Chem Sci Chemistry An Ir-catalyzed intramolecular asymmetric reductive amination (ARA) of bridged biaryl derivatives has been described. Using this unprecedented approach, synthetically useful dibenz[c,e]azepines containing both central and axial chiralities are obtained with excellent enantiocontrol (up to 97% ee). This methodology represents a rare example of enantioselective chemocatalytic synthesis of chiral dibenz[c,e]azepines featuring a broad substrate scope, and their synthetic utilities are exhibited by derivatizing the products into a chiral amino acid derivative and chiral phosphoramidite ligands, which display excellent enantiocontrol in Rh-catalyzed asymmetric hydrogenation of α-dehydroamino acid derivatives. Remarkably, our method is also applicable to enantioselectively synthesize an allocolchicine analogue. Royal Society of Chemistry 2018-12-27 /pmc/articles/PMC6385856/ /pubmed/30881676 http://dx.doi.org/10.1039/c8sc04482a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Yang, Tao
Guo, Xiaochong
Yin, Qin
Zhang, Xumu
Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
title Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
title_full Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
title_fullStr Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
title_full_unstemmed Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
title_short Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
title_sort intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385856/
https://www.ncbi.nlm.nih.gov/pubmed/30881676
http://dx.doi.org/10.1039/c8sc04482a
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AT zhangxumu intramolecularasymmetricreductiveaminationsynthesisofenantioenricheddibenzceazepines