通过手性 N-三氟乙烯磷酰胺催化的不对称还原胺化反应动态解析异构 N-芳基吲哚

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-05-21 DOI:10.1039/D4QO00616J

You-Dong Shao, Dan-Dan Han, Hong-Xin Jiang, Xin-Yu Zhou, Wei-Kang Wang, Jia-Xi Zhang, Ya-Fei Liu and Dao-Juan Cheng

{"title":"通过手性 N-三氟乙烯磷酰胺催化的不对称还原胺化反应动态解析异构 N-芳基吲哚","authors":"You-Dong Shao, Dan-Dan Han, Hong-Xin Jiang, Xin-Yu Zhou, Wei-Kang Wang, Jia-Xi Zhang, Ya-Fei Liu and Dao-Juan Cheng","doi":"10.1039/D4QO00616J","DOIUrl":null,"url":null,"abstract":"The first organocatalyzed asymmetric reductive amination strategy towards C–N axially chiral pentatomic heterobiaryls has been disclosed. The noncovalent n → π* interaction in the cyclic transition state plays a crucial role in ensuring that the reaction occurs through a dynamic kinetic resolution process, leading to a series of N-arylindole atropisomers in good yields and enantioselectivities (up to 96% yield and 91% ee) under the influence of a chiral N-triflyl phosphoramide catalyst.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Dynamic kinetic resolution of atropisomeric N-arylindoles via chiral N-triflyl phosphoramide catalyzed asymmetric reductive amination†\",\"authors\":\"You-Dong Shao, Dan-Dan Han, Hong-Xin Jiang, Xin-Yu Zhou, Wei-Kang Wang, Jia-Xi Zhang, Ya-Fei Liu and Dao-Juan Cheng\",\"doi\":\"10.1039/D4QO00616J\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The first organocatalyzed asymmetric reductive amination strategy towards C–N axially chiral pentatomic heterobiaryls has been disclosed. The noncovalent n → π* interaction in the cyclic transition state plays a crucial role in ensuring that the reaction occurs through a dynamic kinetic resolution process, leading to a series of N-arylindole atropisomers in good yields and enantioselectivities (up to 96% yield and 91% ee) under the influence of a chiral N-triflyl phosphoramide catalyst.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-05-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00616j\",\"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://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00616j","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

首次公开了有机催化的不对称还原胺化策略，可用于 C-N 轴向手性五原子杂环。在手性 N-三乙烯基磷酰胺催化剂的作用下，环状过渡态中的非共价 n→π* 相互作用在确保反应通过动态动力学解析过程发生方面发挥了关键作用，从而以良好的产率和对映体选择性（高达 96% 的产率和 91% 的ee）生成了一系列 N-芳基吲哚异构体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

摘要图片

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Dynamic kinetic resolution of atropisomeric N-arylindoles via chiral N-triflyl phosphoramide catalyzed asymmetric reductive amination†

The first organocatalyzed asymmetric reductive amination strategy towards C–N axially chiral pentatomic heterobiaryls has been disclosed. The noncovalent n → π* interaction in the cyclic transition state plays a crucial role in ensuring that the reaction occurs through a dynamic kinetic resolution process, leading to a series of N-arylindole atropisomers in good yields and enantioselectivities (up to 96% yield and 91% ee) under the influence of a chiral N-triflyl phosphoramide catalyst.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

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.