{"title":"(1R/S,7aS/R)-1-苄基-1-[2,8-双(三氟甲基)喹啉-4-基]-六氢恶唑并[3,4-a]吡啶-3-酮","authors":"Dawid J Kucharski, Przemysław J. Boratyński","doi":"10.3390/m1756","DOIUrl":null,"url":null,"abstract":"An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments.","PeriodicalId":18761,"journal":{"name":"Molbank","volume":" April","pages":""},"PeriodicalIF":0.6000,"publicationDate":"2023-12-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"(1R/S,7aS/R)-1-Benzyl-1-[2,8-bis(trifluoromethyl)quinolin-4-yl]-hexahydro-oxazolo[3,4-a]pyridin-3-one\",\"authors\":\"Dawid J Kucharski, Przemysław J. Boratyński\",\"doi\":\"10.3390/m1756\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments.\",\"PeriodicalId\":18761,\"journal\":{\"name\":\"Molbank\",\"volume\":\" April\",\"pages\":\"\"},\"PeriodicalIF\":0.6000,\"publicationDate\":\"2023-12-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Molbank\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.3390/m1756\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Molbank","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.3390/m1756","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
An unexpected diastereoselective C-alkylation of a mefloquine derivative in up to 57% yield was the result of an attempted Williamson etherification of Boc-mefloquine. The domino reaction involved oxazolidinone ring closure, deprotonation, and stereoselective carbon–carbon bond formation. The structure was confirmed with 2D NMR experiments.
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