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Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives
A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters is disclosed. Various β-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy p...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6685350/ https://www.ncbi.nlm.nih.gov/pubmed/31588293 http://dx.doi.org/10.1039/c9sc02380a |
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author | Chen, Zhi-Min Liu, Jianbo Guo, Jing-Yao Loch, Maximillan DeLuca, Ryan J. Sigman, Matthew S. |
author_facet | Chen, Zhi-Min Liu, Jianbo Guo, Jing-Yao Loch, Maximillan DeLuca, Ryan J. Sigman, Matthew S. |
author_sort | Chen, Zhi-Min |
collection | PubMed |
description | A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters is disclosed. Various β-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy provides rapid access to enantioenriched δ, ε, ζ, and η-alkenyl aryl compounds from simple starting materials. Mechanistic studies suggest that termination of the relay reaction is controlled by affinity of the arene for the Pd complex during migration. |
format | Online Article Text |
id | pubmed-6685350 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-66853502019-10-04 Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives Chen, Zhi-Min Liu, Jianbo Guo, Jing-Yao Loch, Maximillan DeLuca, Ryan J. Sigman, Matthew S. Chem Sci Chemistry A regioselective and enantioselective palladium-catalyzed relay Heck alkenylation of alkenylbenzene derivatives to construct remote stereocenters is disclosed. Various β-substituted styrenes were readily obtained in moderate yields with good to excellent levels of enantioselectivity. This strategy provides rapid access to enantioenriched δ, ε, ζ, and η-alkenyl aryl compounds from simple starting materials. Mechanistic studies suggest that termination of the relay reaction is controlled by affinity of the arene for the Pd complex during migration. Royal Society of Chemistry 2019-06-17 /pmc/articles/PMC6685350/ /pubmed/31588293 http://dx.doi.org/10.1039/c9sc02380a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Chen, Zhi-Min Liu, Jianbo Guo, Jing-Yao Loch, Maximillan DeLuca, Ryan J. Sigman, Matthew S. Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives |
title | Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives
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title_full | Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives
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title_fullStr | Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives
|
title_full_unstemmed | Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives
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title_short | Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives
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title_sort | palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6685350/ https://www.ncbi.nlm.nih.gov/pubmed/31588293 http://dx.doi.org/10.1039/c9sc02380a |
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