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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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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. |
format | Online Article Text |
id | pubmed-8179534 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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