{"title":"3,3-二氟-2-芳基- 3h -吲哚与环酮的不对称曼尼希反应合成c2 -季吲哚-3-酮的高对映选择性和前所未有的非对映选择性","authors":"Hongyu Zhang, , , Qimei Yu, , , Jianfeng Mu, , , Xinjie Liang, , , Xiao Liu, , , Xiaochen Wang, , , Li Tang*, , , Bei Wei*, , and , Shurong Ban*, ","doi":"10.1021/acs.joc.5c01028","DOIUrl":null,"url":null,"abstract":"<p >Described here is a chiral phosphoric acid (CPA)-catalyzed asymmetric Mannich reaction of 3,3-difluoro-2-aryl-3<i>H</i>-indoles with cycloketones to produce C2-quaternary indolin-3-ones. Notable features of this method include: (1) unprecedented diastereoselectivity and high stereoselectivity; (2) access to not-fully-explored diastereomers.</p>","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"90 38","pages":"13754–13760"},"PeriodicalIF":3.6000,"publicationDate":"2025-09-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"High Enantioselective and Unprecedented Diastereoselective Synthesis of C2-Quaternary Indolin-3-ones by CPA-Catalyzed Asymmetric Mannich Reaction of 3,3-Difluoro-2-aryl-3H-indoles with Cycloketones\",\"authors\":\"Hongyu Zhang, , , Qimei Yu, , , Jianfeng Mu, , , Xinjie Liang, , , Xiao Liu, , , Xiaochen Wang, , , Li Tang*, , , Bei Wei*, , and , Shurong Ban*, \",\"doi\":\"10.1021/acs.joc.5c01028\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Described here is a chiral phosphoric acid (CPA)-catalyzed asymmetric Mannich reaction of 3,3-difluoro-2-aryl-3<i>H</i>-indoles with cycloketones to produce C2-quaternary indolin-3-ones. Notable features of this method include: (1) unprecedented diastereoselectivity and high stereoselectivity; (2) access to not-fully-explored diastereomers.</p>\",\"PeriodicalId\":57,\"journal\":{\"name\":\"Journal of Organic Chemistry\",\"volume\":\"90 38\",\"pages\":\"13754–13760\"},\"PeriodicalIF\":3.6000,\"publicationDate\":\"2025-09-11\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.joc.5c01028\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.joc.5c01028","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
High Enantioselective and Unprecedented Diastereoselective Synthesis of C2-Quaternary Indolin-3-ones by CPA-Catalyzed Asymmetric Mannich Reaction of 3,3-Difluoro-2-aryl-3H-indoles with Cycloketones
Described here is a chiral phosphoric acid (CPA)-catalyzed asymmetric Mannich reaction of 3,3-difluoro-2-aryl-3H-indoles with cycloketones to produce C2-quaternary indolin-3-ones. Notable features of this method include: (1) unprecedented diastereoselectivity and high stereoselectivity; (2) access to not-fully-explored diastereomers.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.