{"title":"Asymmetric [4+3] Cycloaddition of Hydroxyphenyl Indolinones to Synthesize Novel Spirooxindoles","authors":"Shuhui Huang, Yongquan Xu, Mohan Li, Lihuan Liao, Weiwu Ren","doi":"10.1039/d5qo00075k","DOIUrl":null,"url":null,"abstract":"The first asymmetric [4+3] cycloaddition of hydroxyphenyl indolinones has been reported to afford a new series of multisubstituted spirooxindole derivatives embedded with an oxadiazepine scaffold with high stereoselectivities. The reaction proceeds via o-QM intermediates produced in situ from hydroxyphenyl indolinones, which could undergo cyclization with azomethine imines under CPA catalysis to deliver a new type of seven-membered spirocyclic oxindole compounds. High yields, exclusive diastereoselectivities, and excellent enantioselectivities as well as wide substrate scope were obtained in this organocatalytic reaction.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"25 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5qo00075k","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The first asymmetric [4+3] cycloaddition of hydroxyphenyl indolinones has been reported to afford a new series of multisubstituted spirooxindole derivatives embedded with an oxadiazepine scaffold with high stereoselectivities. The reaction proceeds via o-QM intermediates produced in situ from hydroxyphenyl indolinones, which could undergo cyclization with azomethine imines under CPA catalysis to deliver a new type of seven-membered spirocyclic oxindole compounds. High yields, exclusive diastereoselectivities, and excellent enantioselectivities as well as wide substrate scope were obtained in this organocatalytic reaction.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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