Peiyao Liang, Siyi Chen, Xin Liu, Shenghan Teng, Shoulei Wang
{"title":"碱促进的亚烷基琥珀酰亚胺级联乙烯基迈克尔/迈克尔加成反应,用于构建五代环戊烷。","authors":"Peiyao Liang, Siyi Chen, Xin Liu, Shenghan Teng, Shoulei Wang","doi":"10.1039/d4ob01455c","DOIUrl":null,"url":null,"abstract":"<p><p>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.</p>","PeriodicalId":2,"journal":{"name":"ACS Applied Bio Materials","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"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\":\"<p><p>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.</p>\",\"PeriodicalId\":2,\"journal\":{\"name\":\"ACS Applied Bio Materials\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-10-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Applied Bio Materials\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4ob01455c\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"MATERIALS SCIENCE, BIOMATERIALS\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Bio Materials","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01455c","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, BIOMATERIALS","Score":null,"Total":0}
Base-promoted cascade vinylogous Michael/Michael addition of alkylidene succinimides for the construction of penta-substituted cyclopentanes.
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.