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- Title
Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution.
- Authors
Hu, Yang; Yuan, Jie; Li, Zheyao; Zhao, Lin; Zhao, Jianhong; Yu, Xinhong
- Abstract
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. 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.
- Subjects
KINETIC resolution; ETHER (Anesthetic); OXINDOLES; OXIDATION; ETHERS
- Publication
Communications Chemistry, 2022, Vol 5, Issue 1, p1
- ISSN
2399-3669
- Publication type
Article
- DOI
10.1038/s42004-022-00695-3