钯催化的N-2,2,2-三氟乙基isatin酮亚胺的不对称(4+3)环加成:获得光学活性螺环吲哚†

Yinggao Meng , Manman Song , Yue Wang , Yuxin Wang , Er-Qing Li
{"title":"钯催化的N-2,2,2-三氟乙基isatin酮亚胺的不对称(4+3)环加成:获得光学活性螺环吲哚†","authors":"Yinggao Meng ,&nbsp;Manman Song ,&nbsp;Yue Wang ,&nbsp;Yuxin Wang ,&nbsp;Er-Qing Li","doi":"10.1039/d3qo00501a","DOIUrl":null,"url":null,"abstract":"<div><p>A palladium-catalyzed asymmetric (4 + 3) cycloaddition of <em>N</em>-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Brønsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 11","pages":"Pages 2648-2652"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles†\",\"authors\":\"Yinggao Meng ,&nbsp;Manman Song ,&nbsp;Yue Wang ,&nbsp;Yuxin Wang ,&nbsp;Er-Qing Li\",\"doi\":\"10.1039/d3qo00501a\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A palladium-catalyzed asymmetric (4 + 3) cycloaddition of <em>N</em>-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Brønsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.</p></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"10 11\",\"pages\":\"Pages 2648-2652\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052411023008131\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023008131","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

报道了钯催化的N-2,2,2-三氟乙基isatin酮亚胺与2-亚甲基三亚甲基碳酸酯的不对称(4+3)环加成反应,以中等产率和良好至优异的ee值对映选择性地得到三氟甲基螺环吲哚。在实验上,反应在没有Brønsted碱的情况下以一锅法顺利进行,这为高效和经济高效地构建光学纯三氟甲基化中型环铺平了道路。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles†

Palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines: access to optically active spirooxindoles†

A palladium-catalyzed asymmetric (4 + 3) cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with 2-methylidenetrimethylene carbonate was reported to enantioselectively afford trifluoromethylated spirooxindoles in moderate yields and good to excellent ee values. Experimentally, the reaction proceeded smoothly in the absence of a Brønsted base in a one-pot manner, which paved a way for efficient and cost-effective construction of optically pure trifluoromethylated medium-sized rings.

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
CiteScore
7.80
自引率
0.00%
发文量
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信