Ji Yang, Zhenni He, Zhen Yao, Wei Huang, Siwen Meng, Lijin Xu, Qing-Hua Fan
{"title":"铑催化喹啉-2-乙醛和苯胺的一锅串联还原胺化/不对称转移加氢高效合成手性邻二胺","authors":"Ji Yang, Zhenni He, Zhen Yao, Wei Huang, Siwen Meng, Lijin Xu, Qing-Hua Fan","doi":"10.1039/d5qo00625b","DOIUrl":null,"url":null,"abstract":"Enantioselective synthesis of chiral <em>N</em>,<em>N</em>′-diaryl vicinal diamines <em>via</em> Cp*Rh-catalyzed one-pot tandem reductive amination/asymmetric transfer hydrogenation of quinoxaline-2-carbaldehydes with anilines using HCO<small><sub>2</sub></small>H/NEt<small><sub>3</sub></small> (5/2) as the reductant has been developed. This mild catalytic system exhibits broad substrate generality and efficiently produces diversely substituted chiral <em>N</em>,<em>N</em>′-diaryl vicinal diamines with opposite configurations in high yields and excellent enantioselectivities (up to >99% ee). The synthetic utility of this protocol has been validated through successful gram-scale synthesis and facile derivatization of the resulting chiral vicinal diamines.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"2 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Rhodium-catalyzed one-pot tandem reductive amination/asymmetric transfer hydrogenation of quinoxaline-2-carbaldehydes and anilines for the efficient synthesis of chiral vicinal diamines\",\"authors\":\"Ji Yang, Zhenni He, Zhen Yao, Wei Huang, Siwen Meng, Lijin Xu, Qing-Hua Fan\",\"doi\":\"10.1039/d5qo00625b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Enantioselective synthesis of chiral <em>N</em>,<em>N</em>′-diaryl vicinal diamines <em>via</em> Cp*Rh-catalyzed one-pot tandem reductive amination/asymmetric transfer hydrogenation of quinoxaline-2-carbaldehydes with anilines using HCO<small><sub>2</sub></small>H/NEt<small><sub>3</sub></small> (5/2) as the reductant has been developed. This mild catalytic system exhibits broad substrate generality and efficiently produces diversely substituted chiral <em>N</em>,<em>N</em>′-diaryl vicinal diamines with opposite configurations in high yields and excellent enantioselectivities (up to >99% ee). The synthetic utility of this protocol has been validated through successful gram-scale synthesis and facile derivatization of the resulting chiral vicinal diamines.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":\"2 1\",\"pages\":\"\"},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2025-05-13\",\"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/d5qo00625b\",\"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/d5qo00625b","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Rhodium-catalyzed one-pot tandem reductive amination/asymmetric transfer hydrogenation of quinoxaline-2-carbaldehydes and anilines for the efficient synthesis of chiral vicinal diamines
Enantioselective synthesis of chiral N,N′-diaryl vicinal diamines via Cp*Rh-catalyzed one-pot tandem reductive amination/asymmetric transfer hydrogenation of quinoxaline-2-carbaldehydes with anilines using HCO2H/NEt3 (5/2) as the reductant has been developed. This mild catalytic system exhibits broad substrate generality and efficiently produces diversely substituted chiral N,N′-diaryl vicinal diamines with opposite configurations in high yields and excellent enantioselectivities (up to >99% ee). The synthetic utility of this protocol has been validated through successful gram-scale synthesis and facile derivatization of the resulting chiral vicinal diamines.
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.