Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution

Chiral benzo five-membered heterocyclic spirocyclopropanes are an important class of parent core structures with pharmacological activity. A novel organocatalytic one-pot cascade ether oxidation iminium-ion activation strategy for the asymmetric spirocyclopropylation of benzofuran-2-ones and indolin...

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Autores principales: Hu, Yang, Yuan, Jie, Li, Zheyao, Zhao, Lin, Zhao, Jianhong, Yu, Xinhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9814566/
https://www.ncbi.nlm.nih.gov/pubmed/36697948
http://dx.doi.org/10.1038/s42004-022-00695-3
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author Hu, Yang
Yuan, Jie
Li, Zheyao
Zhao, Lin
Zhao, Jianhong
Yu, Xinhong
author_facet Hu, Yang
Yuan, Jie
Li, Zheyao
Zhao, Lin
Zhao, Jianhong
Yu, Xinhong
author_sort Hu, Yang
collection PubMed
description Chiral benzo five-membered heterocyclic spirocyclopropanes are an important class of parent core structures with pharmacological activity. A novel organocatalytic one-pot cascade ether oxidation iminium-ion activation strategy for the asymmetric spirocyclopropylation of benzofuran-2-ones and indolin-2-ones from allyl tert-butyl ethers/ pent-2,4-dienyl ethyl ethers with excellent enantioselectivity (ee% up to > 99) and diastereoselectivity(dr.% up to 91:9) has been developed. This process involves the successful dynamic kinetic resolution of racemic 3-bromobenzofuran-2-ones or 3-bromoindolin-2-ones. Its synthetic application will provide a new aminocatalytic cascade tool for the efficient synthesis of complex molecules.
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spelling pubmed-98145662023-01-10 Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution Hu, Yang Yuan, Jie Li, Zheyao Zhao, Lin Zhao, Jianhong Yu, Xinhong Commun Chem Article Chiral benzo five-membered heterocyclic spirocyclopropanes are an important class of parent core structures with pharmacological activity. A novel organocatalytic one-pot cascade ether oxidation iminium-ion activation strategy for the asymmetric spirocyclopropylation of benzofuran-2-ones and indolin-2-ones from allyl tert-butyl ethers/ pent-2,4-dienyl ethyl ethers with excellent enantioselectivity (ee% up to > 99) and diastereoselectivity(dr.% up to 91:9) has been developed. This process involves the successful dynamic kinetic resolution of racemic 3-bromobenzofuran-2-ones or 3-bromoindolin-2-ones. Its synthetic application will provide a new aminocatalytic cascade tool for the efficient synthesis of complex molecules. Nature Publishing Group UK 2022-09-06 /pmc/articles/PMC9814566/ /pubmed/36697948 http://dx.doi.org/10.1038/s42004-022-00695-3 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
Hu, Yang
Yuan, Jie
Li, Zheyao
Zhao, Lin
Zhao, Jianhong
Yu, Xinhong
Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
title Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
title_full Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
title_fullStr Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
title_full_unstemmed Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
title_short Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
title_sort asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9814566/
https://www.ncbi.nlm.nih.gov/pubmed/36697948
http://dx.doi.org/10.1038/s42004-022-00695-3
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