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A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides
A general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, us...
| Autores principales: | , , , , , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Nature Publishing Group UK
2022
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8799647/ https://www.ncbi.nlm.nih.gov/pubmed/35091551 http://dx.doi.org/10.1038/s41467-022-28098-x |
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| author | Jacob, Clément Baguia, Hajar Dubart, Amaury Oger, Samuel Thilmany, Pierre Beaudelot, Jérôme Deldaele, Christopher Peruško, Stefano Landrain, Yohann Michelet, Bastien Neale, Samuel Romero, Eugénie Moucheron, Cécile Van Speybroeck, Veronique Theunissen, Cédric Evano, Gwilherm |
| author_facet | Jacob, Clément Baguia, Hajar Dubart, Amaury Oger, Samuel Thilmany, Pierre Beaudelot, Jérôme Deldaele, Christopher Peruško, Stefano Landrain, Yohann Michelet, Bastien Neale, Samuel Romero, Eugénie Moucheron, Cécile Van Speybroeck, Veronique Theunissen, Cédric Evano, Gwilherm |
| author_sort | Jacob, Clément |
| collection | PubMed |
| description | A general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, useful building blocks in natural product synthesis and medicinal chemistry, with full control of the regioselectivity of the cyclization resulting from a unique and underrated radical 4-exo-dig pathway. |
| format | Online Article Text |
| id | pubmed-8799647 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | Nature Publishing Group UK |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-87996472022-02-07 A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides Jacob, Clément Baguia, Hajar Dubart, Amaury Oger, Samuel Thilmany, Pierre Beaudelot, Jérôme Deldaele, Christopher Peruško, Stefano Landrain, Yohann Michelet, Bastien Neale, Samuel Romero, Eugénie Moucheron, Cécile Van Speybroeck, Veronique Theunissen, Cédric Evano, Gwilherm Nat Commun Article A general anti-Baldwin radical 4-exo-dig cyclization from nitrogen-substituted alkynes is reported. Upon reaction with a heteroleptic copper complex in the presence of an amine and under visible light irradiation, a range of ynamides were shown to smoothly cyclize to the corresponding azetidines, useful building blocks in natural product synthesis and medicinal chemistry, with full control of the regioselectivity of the cyclization resulting from a unique and underrated radical 4-exo-dig pathway. Nature Publishing Group UK 2022-01-28 /pmc/articles/PMC8799647/ /pubmed/35091551 http://dx.doi.org/10.1038/s41467-022-28098-x Text en © The Author(s) 2022 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 Jacob, Clément Baguia, Hajar Dubart, Amaury Oger, Samuel Thilmany, Pierre Beaudelot, Jérôme Deldaele, Christopher Peruško, Stefano Landrain, Yohann Michelet, Bastien Neale, Samuel Romero, Eugénie Moucheron, Cécile Van Speybroeck, Veronique Theunissen, Cédric Evano, Gwilherm A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides |
| title | A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides |
| title_full | A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides |
| title_fullStr | A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides |
| title_full_unstemmed | A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides |
| title_short | A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides |
| title_sort | general synthesis of azetidines by copper-catalysed photoinduced anti-baldwin radical cyclization of ynamides |
| topic | Article |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8799647/ https://www.ncbi.nlm.nih.gov/pubmed/35091551 http://dx.doi.org/10.1038/s41467-022-28098-x |
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