Peiyao Liang , Siyi Chen , Xin Liu , Shenghan Teng , Shoulei Wang
{"title":"Base-promoted cascade vinylogous Michael/Michael addition of alkylidene succinimides for the construction of penta-substituted cyclopentanes†","authors":"Peiyao Liang , Siyi Chen , Xin Liu , Shenghan Teng , Shoulei Wang","doi":"10.1039/d4ob01455c","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, an efficient, base catalyzed cascade vinylogous Michael/Michael cycloaddition reaction of α-alkylidene succinimides and oxindole-derived pyrazolones has been successfully developed. A variety of highly functionalized cyclopentanes fused with spirooxindoles were obtained in good yields, with excellent diastereoselectivities and exclusive vinylogous site-selectivities. This strategy represents the first example of α-alkylidene succinimides serving as nucleophilic reagents to trigger a vinylogous cascade reaction.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"22 45","pages":"Pages 8832-8837"},"PeriodicalIF":2.7000,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024009108","RegionNum":3,"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
Herein, an efficient, base catalyzed cascade vinylogous Michael/Michael cycloaddition reaction of α-alkylidene succinimides and oxindole-derived pyrazolones has been successfully developed. A variety of highly functionalized cyclopentanes fused with spirooxindoles were obtained in good yields, with excellent diastereoselectivities and exclusive vinylogous site-selectivities. This strategy represents the first example of α-alkylidene succinimides serving as nucleophilic reagents to trigger a vinylogous cascade reaction.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.