Deli Gan, Sumei Zhao, Min Yang, Minghui Xu, Bin Chen, Wenhao Yu, Hai-Liang Ni, Bi-Qin Wang, Ping Hu, Peng Cao
{"title":"铱催化的乙烯基叠氮化物和乙烯基苯并噁嗪酮的高对映选择性和化学发散性偶联反应","authors":"Deli Gan, Sumei Zhao, Min Yang, Minghui Xu, Bin Chen, Wenhao Yu, Hai-Liang Ni, Bi-Qin Wang, Ping Hu, Peng Cao","doi":"10.1039/d4qo01862a","DOIUrl":null,"url":null,"abstract":"The first Iridium-catalyzed enantioselective coupling reaction of vinyl azides and vinyl benzoxazinones is presented. Vinyl azides underwent a tandem allylic alkylation/interrupted Schmidt rearrangement process to produce enantioenriched 3,4-dihydroquinolin-2(1H)-imines, a new class of N-heterocyles. In the presence of CH3CO2H, a conventional asymmetric allylic substitution occurred to provide access to nonracemic allylic amides. The synthetic transformations of product were implemented to construct chiral amine, amide and N-hetero polycycle.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Iridium-Catalyzed Highly Enantioselective and Chemodivergent Coupling Reaction of Vinyl Azides and Vinyl Benzoxazinones\",\"authors\":\"Deli Gan, Sumei Zhao, Min Yang, Minghui Xu, Bin Chen, Wenhao Yu, Hai-Liang Ni, Bi-Qin Wang, Ping Hu, Peng Cao\",\"doi\":\"10.1039/d4qo01862a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The first Iridium-catalyzed enantioselective coupling reaction of vinyl azides and vinyl benzoxazinones is presented. Vinyl azides underwent a tandem allylic alkylation/interrupted Schmidt rearrangement process to produce enantioenriched 3,4-dihydroquinolin-2(1H)-imines, a new class of N-heterocyles. In the presence of CH3CO2H, a conventional asymmetric allylic substitution occurred to provide access to nonracemic allylic amides. The synthetic transformations of product were implemented to construct chiral amine, amide and N-hetero polycycle.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-11-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4qo01862a\",\"RegionNum\":1,\"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":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01862a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Iridium-Catalyzed Highly Enantioselective and Chemodivergent Coupling Reaction of Vinyl Azides and Vinyl Benzoxazinones
The first Iridium-catalyzed enantioselective coupling reaction of vinyl azides and vinyl benzoxazinones is presented. Vinyl azides underwent a tandem allylic alkylation/interrupted Schmidt rearrangement process to produce enantioenriched 3,4-dihydroquinolin-2(1H)-imines, a new class of N-heterocyles. In the presence of CH3CO2H, a conventional asymmetric allylic substitution occurred to provide access to nonracemic allylic amides. The synthetic transformations of product were implemented to construct chiral amine, amide and N-hetero polycycle.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
