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Organocatalytic atroposelective synthesis of axially chiral styrenes

Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of the most abundant and principal feedstocks and thus represent excellent prospective building blocks for chemica...

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Autores principales: Zheng, Sheng-Cai, Wu, San, Zhou, Qinghai, Chung, Lung Wa, Ye, Liu, Tan, Bin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5418600/
https://www.ncbi.nlm.nih.gov/pubmed/28466872
http://dx.doi.org/10.1038/ncomms15238
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author Zheng, Sheng-Cai
Wu, San
Zhou, Qinghai
Chung, Lung Wa
Ye, Liu
Tan, Bin
author_facet Zheng, Sheng-Cai
Wu, San
Zhou, Qinghai
Chung, Lung Wa
Ye, Liu
Tan, Bin
author_sort Zheng, Sheng-Cai
collection PubMed
description Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of the most abundant and principal feedstocks and thus represent excellent prospective building blocks for chemical synthesis. Driven by the development of atroposelective synthesis of axially chiral styrene derivatives, we discovered herein the asymmetric organocatalytic approach via direct Michael addition reaction of substituted diones/ketone esters/malononitrile to alkynals. The axially chiral styrene compounds were produced with good chemical yields, enantioselectivities and almost complete E/Z-selectivities through a secondary amine-catalysed iminium activation strategy under mild conditions. Such structural motifs are important precursors for further transformations into biologically active compounds and synthetic useful intermediates and may have potential applications in asymmetric synthesis as olefin ligands or organocatalysts.
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spelling pubmed-54186002017-07-06 Organocatalytic atroposelective synthesis of axially chiral styrenes Zheng, Sheng-Cai Wu, San Zhou, Qinghai Chung, Lung Wa Ye, Liu Tan, Bin Nat Commun Article Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of the most abundant and principal feedstocks and thus represent excellent prospective building blocks for chemical synthesis. Driven by the development of atroposelective synthesis of axially chiral styrene derivatives, we discovered herein the asymmetric organocatalytic approach via direct Michael addition reaction of substituted diones/ketone esters/malononitrile to alkynals. The axially chiral styrene compounds were produced with good chemical yields, enantioselectivities and almost complete E/Z-selectivities through a secondary amine-catalysed iminium activation strategy under mild conditions. Such structural motifs are important precursors for further transformations into biologically active compounds and synthetic useful intermediates and may have potential applications in asymmetric synthesis as olefin ligands or organocatalysts. Nature Publishing Group 2017-05-03 /pmc/articles/PMC5418600/ /pubmed/28466872 http://dx.doi.org/10.1038/ncomms15238 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Zheng, Sheng-Cai
Wu, San
Zhou, Qinghai
Chung, Lung Wa
Ye, Liu
Tan, Bin
Organocatalytic atroposelective synthesis of axially chiral styrenes
title Organocatalytic atroposelective synthesis of axially chiral styrenes
title_full Organocatalytic atroposelective synthesis of axially chiral styrenes
title_fullStr Organocatalytic atroposelective synthesis of axially chiral styrenes
title_full_unstemmed Organocatalytic atroposelective synthesis of axially chiral styrenes
title_short Organocatalytic atroposelective synthesis of axially chiral styrenes
title_sort organocatalytic atroposelective synthesis of axially chiral styrenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5418600/
https://www.ncbi.nlm.nih.gov/pubmed/28466872
http://dx.doi.org/10.1038/ncomms15238
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