Xiaowei Han, Yue Zhao, Zhuangzhi Shi , Minyan Wang
{"title":"铑催化的宝石二氟烯与苯胺的不对称氢胺化反应","authors":"Xiaowei Han, Yue Zhao, Zhuangzhi Shi , Minyan Wang","doi":"10.1016/j.tchem.2022.100023","DOIUrl":null,"url":null,"abstract":"<div><p>A rhodium-catalyzed protocol has been established for the enantioselective hydroamination of <em>gem</em>-difluoroallenes with anilines. This strategy shows complete atom-efficiency to access a variety of enantioenriched <em>gem</em>-difluoroallylic amines in excellent branched selectivity (>99:1 for each case), which are important backbones in many biologically active compounds. Mechanistic studies suggest the generation of a <em>gem</em>-difluoro π-allyl rhodium intermediate by an exclusive hydrometalation pathway, which undergoes nucleophilic substitution of amines.</p></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"3 ","pages":"Article 100023"},"PeriodicalIF":0.0000,"publicationDate":"2022-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S2666951X22000195/pdfft?md5=e25b8e0bd6924ba768de00837468f251&pid=1-s2.0-S2666951X22000195-main.pdf","citationCount":"0","resultStr":"{\"title\":\"Rhodium-catalyzed asymmetric hydroamination of gem-difluoroallenes with anilines\",\"authors\":\"Xiaowei Han, Yue Zhao, Zhuangzhi Shi , Minyan Wang\",\"doi\":\"10.1016/j.tchem.2022.100023\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A rhodium-catalyzed protocol has been established for the enantioselective hydroamination of <em>gem</em>-difluoroallenes with anilines. This strategy shows complete atom-efficiency to access a variety of enantioenriched <em>gem</em>-difluoroallylic amines in excellent branched selectivity (>99:1 for each case), which are important backbones in many biologically active compounds. Mechanistic studies suggest the generation of a <em>gem</em>-difluoro π-allyl rhodium intermediate by an exclusive hydrometalation pathway, which undergoes nucleophilic substitution of amines.</p></div>\",\"PeriodicalId\":74918,\"journal\":{\"name\":\"Tetrahedron chem\",\"volume\":\"3 \",\"pages\":\"Article 100023\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2022-08-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.sciencedirect.com/science/article/pii/S2666951X22000195/pdfft?md5=e25b8e0bd6924ba768de00837468f251&pid=1-s2.0-S2666951X22000195-main.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron chem\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666951X22000195\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron chem","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666951X22000195","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Rhodium-catalyzed asymmetric hydroamination of gem-difluoroallenes with anilines
A rhodium-catalyzed protocol has been established for the enantioselective hydroamination of gem-difluoroallenes with anilines. This strategy shows complete atom-efficiency to access a variety of enantioenriched gem-difluoroallylic amines in excellent branched selectivity (>99:1 for each case), which are important backbones in many biologically active compounds. Mechanistic studies suggest the generation of a gem-difluoro π-allyl rhodium intermediate by an exclusive hydrometalation pathway, which undergoes nucleophilic substitution of amines.
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