Yinggao Meng , Manman Song , Yue Wang , Yuxin Wang , Er-Qing Li
{"title":"钯催化的N-2,2,2-三氟乙基isatin酮亚胺的不对称(4+3)环加成:获得光学活性螺环吲哚†","authors":"Yinggao Meng , Manman Song , Yue Wang , Yuxin Wang , Er-Qing Li","doi":"10.1039/d3qo00501a","DOIUrl":null,"url":null,"abstract":"<div><p>A palladium-catalyzed asymmetric (4 + 3) cycloaddition of <em>N</em>-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Brønsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 11","pages":"Pages 2648-2652"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles†\",\"authors\":\"Yinggao Meng , Manman Song , Yue Wang , Yuxin Wang , Er-Qing Li\",\"doi\":\"10.1039/d3qo00501a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A palladium-catalyzed asymmetric (4 + 3) cycloaddition of <em>N</em>-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Brønsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 11\",\"pages\":\"Pages 2648-2652\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052411023008131\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023008131","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles†
A palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Brønsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.