{"title":"三氟化硼镱催化的芳基氨基甲基取代的供体-受体环丙烷分子内芳基化开环:获得四氢喹啉","authors":"Thangaraj Devaraj, Kannupal Srinivasan","doi":"10.1021/acs.joc.4c00924","DOIUrl":null,"url":null,"abstract":"The treatment of arylaminomethyl-substituted donor–acceptor cyclopropanes with a catalytic amount of Yb(OTf)<sub>3</sub> provides expedient access to tetrahydroquinoline derivatives. The transformation proceeds through an intramolecular S<sub>N</sub>2-type attack of the aminomethyl-containing aryl ring on the cyclopropane ring, leading to the formation of the products as single diastereomers.","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Ytterbium Triflate-Catalyzed Intramolecular Arylative Ring Opening of Arylaminomethyl-Substituted Donor–Acceptor Cyclopropanes: Access to Tetrahydroquinolines\",\"authors\":\"Thangaraj Devaraj, Kannupal Srinivasan\",\"doi\":\"10.1021/acs.joc.4c00924\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The treatment of arylaminomethyl-substituted donor–acceptor cyclopropanes with a catalytic amount of Yb(OTf)<sub>3</sub> provides expedient access to tetrahydroquinoline derivatives. The transformation proceeds through an intramolecular S<sub>N</sub>2-type attack of the aminomethyl-containing aryl ring on the cyclopropane ring, leading to the formation of the products as single diastereomers.\",\"PeriodicalId\":57,\"journal\":{\"name\":\"The Journal of Organic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-09-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The Journal of Organic Chemistry\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.joc.4c00924\",\"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":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c00924","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Ytterbium Triflate-Catalyzed Intramolecular Arylative Ring Opening of Arylaminomethyl-Substituted Donor–Acceptor Cyclopropanes: Access to Tetrahydroquinolines
The treatment of arylaminomethyl-substituted donor–acceptor cyclopropanes with a catalytic amount of Yb(OTf)3 provides expedient access to tetrahydroquinoline derivatives. The transformation proceeds through an intramolecular SN2-type attack of the aminomethyl-containing aryl ring on the cyclopropane ring, leading to the formation of the products as single diastereomers.
期刊介绍:
The 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.