文献类型：期刊文献

英文题名：Asymmetric α-spirocyclopropanation of oxindoles and benzofuranones via dynamic kinetic resolution

作者：Hu, Yang[1,2];Yuan, Jie[1,2];Li, Zheyao[1,2];Zhao, Lin[1,2];Zhao, Jianhong[1,2];Yu, Xinhong[1,2]

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai, Peoples R China;[2]East China Univ Sci & Technol, State Key Lab Bioengn Reactors, Shanghai 200237, Peoples R China

年份：2022

卷号：5

期号：1

外文期刊名：COMMUNICATIONS CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000850556000002)】；

基金：We gratefully acknowledge financial support from the National Science Foundation of China (20972051 and 21476078, X.-H.Y.), (08431901800 and 08430703900, X.-H. Y.).

语种：英文

摘要：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.