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Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles

A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial subs...

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Autores principales: Fan, Guodong, Wang, Qingyun, Xu, Jun, Zheng, Pengcheng, Chi, Yonggui Robin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10349821/
https://www.ncbi.nlm.nih.gov/pubmed/37454112
http://dx.doi.org/10.1038/s41467-023-39988-z
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author Fan, Guodong
Wang, Qingyun
Xu, Jun
Zheng, Pengcheng
Chi, Yonggui Robin
author_facet Fan, Guodong
Wang, Qingyun
Xu, Jun
Zheng, Pengcheng
Chi, Yonggui Robin
author_sort Fan, Guodong
collection PubMed
description A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial substrates. Mechanistic studies via experiments suggest that our chemoselectivity controls are mostly achieved on the reducing properties of different sited Breslow intermediates. Several side reactions processes and the corresponding side adducts are also studied by high resolution mass spectroscopy analysis. Our method allows for efficient assembly of the furo[2,3-b]pyrrole structural moieties and their analogues widely found in natural products and pharmaceuticals.
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spelling pubmed-103498212023-07-17 Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles Fan, Guodong Wang, Qingyun Xu, Jun Zheng, Pengcheng Chi, Yonggui Robin Nat Commun Article A carbene-catalyzed chemoselective reaction of unsymmetric enedials is disclosed. The reaction provides a concise access to bicyclic furo[2,3-b]pyrroles derivatives in excellent selectivity. A main challenge in this reaction is chemoselective reaction of the two aldehyde moieties in the enedial substrates. Mechanistic studies via experiments suggest that our chemoselectivity controls are mostly achieved on the reducing properties of different sited Breslow intermediates. Several side reactions processes and the corresponding side adducts are also studied by high resolution mass spectroscopy analysis. Our method allows for efficient assembly of the furo[2,3-b]pyrrole structural moieties and their analogues widely found in natural products and pharmaceuticals. Nature Publishing Group UK 2023-07-15 /pmc/articles/PMC10349821/ /pubmed/37454112 http://dx.doi.org/10.1038/s41467-023-39988-z 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
Fan, Guodong
Wang, Qingyun
Xu, Jun
Zheng, Pengcheng
Chi, Yonggui Robin
Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_full Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_fullStr Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_full_unstemmed Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_short Carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to Furo[2,3-b]pyrroles
title_sort carbene-catalyzed chemoselective reaction of unsymmetric enedials for access to furo[2,3-b]pyrroles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10349821/
https://www.ncbi.nlm.nih.gov/pubmed/37454112
http://dx.doi.org/10.1038/s41467-023-39988-z
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