Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution
Chiral benzo five-membered heterocyclic spirocyclopropanes are pharmacologically active scaffolds, but access to spiral rings with multiple stereocenters is challenging. Here, the authors report an organocatalytic one-pot cascade ether oxidation iminium-ion activation strategy for the asymmetric spi...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2022-09-01
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| Series: | Communications Chemistry |
| Online Access: | https://doi.org/10.1038/s42004-022-00695-3 |
| _version_ | 1811211559172571136 |
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| author | Yang Hu Jie Yuan Zheyao Li Lin Zhao Jianhong Zhao Xinhong Yu |
| author_facet | Yang Hu Jie Yuan Zheyao Li Lin Zhao Jianhong Zhao Xinhong Yu |
| author_sort | Yang Hu |
| collection | DOAJ |
| description | Chiral benzo five-membered heterocyclic spirocyclopropanes are pharmacologically active scaffolds, but access to spiral rings with multiple stereocenters is challenging. Here, the authors report an organocatalytic one-pot cascade ether oxidation iminium-ion activation strategy for the asymmetric spirocyclopropylation of benzofuran-2-ones and indolin-2-ones with excellent enantio- and diastereoselectivity. |
| first_indexed | 2024-04-12T05:14:49Z |
| format | Article |
| id | doaj.art-843941eaf19641f391c2be8723946c16 |
| institution | Directory Open Access Journal |
| issn | 2399-3669 |
| language | English |
| last_indexed | 2024-04-12T05:14:49Z |
| publishDate | 2022-09-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Communications Chemistry |
| spelling | doaj.art-843941eaf19641f391c2be8723946c162022-12-22T03:46:39ZengNature PortfolioCommunications Chemistry2399-36692022-09-01511610.1038/s42004-022-00695-3Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolutionYang Hu0Jie Yuan1Zheyao Li2Lin Zhao3Jianhong Zhao4Xinhong Yu5Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & TechnologyEngineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & TechnologyEngineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & TechnologyEngineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & TechnologyEngineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & TechnologyEngineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science & TechnologyChiral benzo five-membered heterocyclic spirocyclopropanes are pharmacologically active scaffolds, but access to spiral rings with multiple stereocenters is challenging. Here, the authors report an organocatalytic one-pot cascade ether oxidation iminium-ion activation strategy for the asymmetric spirocyclopropylation of benzofuran-2-ones and indolin-2-ones with excellent enantio- and diastereoselectivity.https://doi.org/10.1038/s42004-022-00695-3 |
| spellingShingle | Yang Hu Jie Yuan Zheyao Li Lin Zhao Jianhong Zhao Xinhong Yu Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution Communications Chemistry |
| 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 |
| url | https://doi.org/10.1038/s42004-022-00695-3 |
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