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Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides
Secondary amides are omnipresent structural motifs in peptides, natural products, pharmaceuticals, and agrochemicals. The copper-catalyzed enantioselective hydroaminocarbonylation of alkenes described in this study provides a direct and practical approach for the construction of α-chiral secondary a...
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/PMC8494041/ https://www.ncbi.nlm.nih.gov/pubmed/34703553 http://dx.doi.org/10.1039/d1sc04210f |
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author | Yuan, Yang Zhao, Fengqian Wu, Xiao-Feng |
author_facet | Yuan, Yang Zhao, Fengqian Wu, Xiao-Feng |
author_sort | Yuan, Yang |
collection | PubMed |
description | Secondary amides are omnipresent structural motifs in peptides, natural products, pharmaceuticals, and agrochemicals. The copper-catalyzed enantioselective hydroaminocarbonylation of alkenes described in this study provides a direct and practical approach for the construction of α-chiral secondary amides. An electrophilic amine transfer reagent possessing a 4-(dimethylamino)benzoate group was the key to the success. This method also features broad functional group tolerance and proceeds under very mild conditions, affording a set of α-chiral secondary amides in high yields (up to 96% yield) with unprecedented levels of enantioselectivity (up to >99% ee). α,β-Unsaturated secondary amides can also be produced though the method by using alkynes as the substrate. |
format | Online Article Text |
id | pubmed-8494041 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-84940412021-10-25 Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides Yuan, Yang Zhao, Fengqian Wu, Xiao-Feng Chem Sci Chemistry Secondary amides are omnipresent structural motifs in peptides, natural products, pharmaceuticals, and agrochemicals. The copper-catalyzed enantioselective hydroaminocarbonylation of alkenes described in this study provides a direct and practical approach for the construction of α-chiral secondary amides. An electrophilic amine transfer reagent possessing a 4-(dimethylamino)benzoate group was the key to the success. This method also features broad functional group tolerance and proceeds under very mild conditions, affording a set of α-chiral secondary amides in high yields (up to 96% yield) with unprecedented levels of enantioselectivity (up to >99% ee). α,β-Unsaturated secondary amides can also be produced though the method by using alkynes as the substrate. The Royal Society of Chemistry 2021-08-25 /pmc/articles/PMC8494041/ /pubmed/34703553 http://dx.doi.org/10.1039/d1sc04210f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Yuan, Yang Zhao, Fengqian Wu, Xiao-Feng Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
title | Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
title_full | Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
title_fullStr | Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
title_full_unstemmed | Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
title_short | Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
title_sort | copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8494041/ https://www.ncbi.nlm.nih.gov/pubmed/34703553 http://dx.doi.org/10.1039/d1sc04210f |
work_keys_str_mv | AT yuanyang coppercatalyzedenantioselectivecarbonylationtowardachiralsecondaryamides AT zhaofengqian coppercatalyzedenantioselectivecarbonylationtowardachiralsecondaryamides AT wuxiaofeng coppercatalyzedenantioselectivecarbonylationtowardachiralsecondaryamides |