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Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation

A novel method by a one-step introduction of axial chirality and sterically hindered group has been developed for facile synthesis of axially chiral styrene-type carboxylic acids. With the palladium-catalyzed C–H arylation and olefination of readily available cinnamic acid established, this transfor...

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Autores principales: Yang, Chi, Wu, Tian-Rui, Li, Yan, Wu, Bing-Bing, Jin, Ruo-Xing, Hu, Duo-Duo, Li, Yuan-Bo, Bian, Kang-Jie, Wang, Xi-Sheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179534/
https://www.ncbi.nlm.nih.gov/pubmed/34163646
http://dx.doi.org/10.1039/d0sc06661c
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author Yang, Chi
Wu, Tian-Rui
Li, Yan
Wu, Bing-Bing
Jin, Ruo-Xing
Hu, Duo-Duo
Li, Yuan-Bo
Bian, Kang-Jie
Wang, Xi-Sheng
author_facet Yang, Chi
Wu, Tian-Rui
Li, Yan
Wu, Bing-Bing
Jin, Ruo-Xing
Hu, Duo-Duo
Li, Yuan-Bo
Bian, Kang-Jie
Wang, Xi-Sheng
author_sort Yang, Chi
collection PubMed
description A novel method by a one-step introduction of axial chirality and sterically hindered group has been developed for facile synthesis of axially chiral styrene-type carboxylic acids. With the palladium-catalyzed C–H arylation and olefination of readily available cinnamic acid established, this transformation demonstrated excellent yield, excellent stereocontrol (up to 99% yield and 99% ee), and broad substrate scope under mild conditions. The axially chiral styrene-type carboxylic acids produced have been successfully applied to Cp*Co(III)-catalyzed asymmetric C–H activation reactions, indicating their potential as chiral ligands or catalysts in asymmetric synthesis.
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spelling pubmed-81795342021-06-22 Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation Yang, Chi Wu, Tian-Rui Li, Yan Wu, Bing-Bing Jin, Ruo-Xing Hu, Duo-Duo Li, Yuan-Bo Bian, Kang-Jie Wang, Xi-Sheng Chem Sci Chemistry A novel method by a one-step introduction of axial chirality and sterically hindered group has been developed for facile synthesis of axially chiral styrene-type carboxylic acids. With the palladium-catalyzed C–H arylation and olefination of readily available cinnamic acid established, this transformation demonstrated excellent yield, excellent stereocontrol (up to 99% yield and 99% ee), and broad substrate scope under mild conditions. The axially chiral styrene-type carboxylic acids produced have been successfully applied to Cp*Co(III)-catalyzed asymmetric C–H activation reactions, indicating their potential as chiral ligands or catalysts in asymmetric synthesis. The Royal Society of Chemistry 2021-01-20 /pmc/articles/PMC8179534/ /pubmed/34163646 http://dx.doi.org/10.1039/d0sc06661c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Yang, Chi
Wu, Tian-Rui
Li, Yan
Wu, Bing-Bing
Jin, Ruo-Xing
Hu, Duo-Duo
Li, Yuan-Bo
Bian, Kang-Jie
Wang, Xi-Sheng
Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
title Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
title_full Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
title_fullStr Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
title_full_unstemmed Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
title_short Facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric C–H activation
title_sort facile synthesis of axially chiral styrene-type carboxylic acids via palladium-catalyzed asymmetric c–h activation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179534/
https://www.ncbi.nlm.nih.gov/pubmed/34163646
http://dx.doi.org/10.1039/d0sc06661c
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