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Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
Transition-metal catalyzed asymmetric cyclization of 1,6-enynes has emerged as a powerful method for the construction of carbocycles and heterocycles. However, very rare examples worked under electrochemical conditions. We report herein a Co-catalyzed enantioselective intramolecular reductive coupli...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9998880/ https://www.ncbi.nlm.nih.gov/pubmed/36894526 http://dx.doi.org/10.1038/s41467-023-36704-9 |
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author | Gao, Shiquan Wang, Chen Yang, Junfeng Zhang, Junliang |
author_facet | Gao, Shiquan Wang, Chen Yang, Junfeng Zhang, Junliang |
author_sort | Gao, Shiquan |
collection | PubMed |
description | Transition-metal catalyzed asymmetric cyclization of 1,6-enynes has emerged as a powerful method for the construction of carbocycles and heterocycles. However, very rare examples worked under electrochemical conditions. We report herein a Co-catalyzed enantioselective intramolecular reductive coupling of enynes via electrochemistry using H(2)O as hydride source. The products were obtained in good yields with high regio- and enantioselectivities. It represents the rare progress on the cobalt-catalyzed enantioselective transformation via electrochemistry with a general substrate scope. DFT studies explored the possible reaction pathways and revealed that the oxidative cyclization of enynes by LCo(I) is more favorable than oxidative addition of H(2)O or other pathways. |
format | Online Article Text |
id | pubmed-9998880 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-99988802023-03-11 Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry Gao, Shiquan Wang, Chen Yang, Junfeng Zhang, Junliang Nat Commun Article Transition-metal catalyzed asymmetric cyclization of 1,6-enynes has emerged as a powerful method for the construction of carbocycles and heterocycles. However, very rare examples worked under electrochemical conditions. We report herein a Co-catalyzed enantioselective intramolecular reductive coupling of enynes via electrochemistry using H(2)O as hydride source. The products were obtained in good yields with high regio- and enantioselectivities. It represents the rare progress on the cobalt-catalyzed enantioselective transformation via electrochemistry with a general substrate scope. DFT studies explored the possible reaction pathways and revealed that the oxidative cyclization of enynes by LCo(I) is more favorable than oxidative addition of H(2)O or other pathways. Nature Publishing Group UK 2023-03-09 /pmc/articles/PMC9998880/ /pubmed/36894526 http://dx.doi.org/10.1038/s41467-023-36704-9 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Gao, Shiquan Wang, Chen Yang, Junfeng Zhang, Junliang Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry |
title | Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry |
title_full | Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry |
title_fullStr | Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry |
title_full_unstemmed | Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry |
title_short | Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry |
title_sort | cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9998880/ https://www.ncbi.nlm.nih.gov/pubmed/36894526 http://dx.doi.org/10.1038/s41467-023-36704-9 |
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