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Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis

The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a...

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Autores principales: Xiao, Xiao, Chen, Biao, Yao, Yi-Ping, Zhou, Hai-Jie, Wang, Xu, Wang, Neng-Zhong, Chen, Fen-Er
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9572367/
https://www.ncbi.nlm.nih.gov/pubmed/36235120
http://dx.doi.org/10.3390/molecules27196583
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author Xiao, Xiao
Chen, Biao
Yao, Yi-Ping
Zhou, Hai-Jie
Wang, Xu
Wang, Neng-Zhong
Chen, Fen-Er
author_facet Xiao, Xiao
Chen, Biao
Yao, Yi-Ping
Zhou, Hai-Jie
Wang, Xu
Wang, Neng-Zhong
Chen, Fen-Er
author_sort Xiao, Xiao
collection PubMed
description The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a range of catalytic atroposelective approaches has been reported for the efficient construction of these challenging scaffolds. However, greatly concise and highly useful methodologies for the synthesis of these atropisomeric compounds, focusing on transition-metal, chiral amine, and phosphoric acid catalysis reactions, etc., are still desirable. Hence, it is indispensable to succinctly and systematically present all such reports by means of disclosing the mechanistic analysis and application, as well as the challenges and issues associated with the establishment of these atropisomers. In this review, we summarize the development of catalytic asymmetric synthetic strategies to access non-biaryl atropisomers rotating around a C–N chiral axis, including the reaction methods, mechanism, late-stage transformations, and applications.
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spelling pubmed-95723672022-10-17 Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis Xiao, Xiao Chen, Biao Yao, Yi-Ping Zhou, Hai-Jie Wang, Xu Wang, Neng-Zhong Chen, Fen-Er Molecules Review The significant scaffold offered by atropisomeric amides with a C–N chiral axis has been extensively utilized for pharmaceuticals, agricultural science, and organic syntheses. As a result, the field of atropisomer synthesis has attracted considerable interest within chemistry communities. To date, a range of catalytic atroposelective approaches has been reported for the efficient construction of these challenging scaffolds. However, greatly concise and highly useful methodologies for the synthesis of these atropisomeric compounds, focusing on transition-metal, chiral amine, and phosphoric acid catalysis reactions, etc., are still desirable. Hence, it is indispensable to succinctly and systematically present all such reports by means of disclosing the mechanistic analysis and application, as well as the challenges and issues associated with the establishment of these atropisomers. In this review, we summarize the development of catalytic asymmetric synthetic strategies to access non-biaryl atropisomers rotating around a C–N chiral axis, including the reaction methods, mechanism, late-stage transformations, and applications. MDPI 2022-10-04 /pmc/articles/PMC9572367/ /pubmed/36235120 http://dx.doi.org/10.3390/molecules27196583 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
Xiao, Xiao
Chen, Biao
Yao, Yi-Ping
Zhou, Hai-Jie
Wang, Xu
Wang, Neng-Zhong
Chen, Fen-Er
Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis
title Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis
title_full Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis
title_fullStr Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis
title_full_unstemmed Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis
title_short Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C–N Axis via Enantioselective Catalysis
title_sort construction of non-biaryl atropisomeric amide scaffolds bearing a c–n axis via enantioselective catalysis
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9572367/
https://www.ncbi.nlm.nih.gov/pubmed/36235120
http://dx.doi.org/10.3390/molecules27196583
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