卤化马来酰亚胺的对映选择性和发散性反应。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-14 DOI:10.1021/acs.orglett.5c01444

Jonas Faghtmann,Anne Rask Østergaard,Fabien Fritz,Signe Sofie Pladsbjerg Andresen,Karl Anker Jørgensen

{"title":"卤化马来酰亚胺的对映选择性和发散性反应。","authors":"Jonas Faghtmann,Anne Rask Østergaard,Fabien Fritz,Signe Sofie Pladsbjerg Andresen,Karl Anker Jørgensen","doi":"10.1021/acs.orglett.5c01444","DOIUrl":null,"url":null,"abstract":"Halogenated maleimides can undergo either a [4 + 2] cycloaddition or a [4 + 2]/SN2 cascade reaction in an enantioselective and divergent fashion with catalytically formed trienamines. Under mild acidic conditions, [4 + 2] cycloadducts are isolated in good yields with complete diastereoselectivity and high enantioselectivity. With the addition of silver(I) benzoate as a base, a [4 + 2]/SN2 cascade reaction is induced, forming tricyclic norcaranes in moderate to good yields and with excellent overall stereoselectivity. The influence of the halogen effect on the cycloaddition was investigated experimentally, revealing a minimal impact.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"58 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enantioselective and Divergent Trienamine-Mediated Reactions of Halogenated Maleimides.\",\"authors\":\"Jonas Faghtmann,Anne Rask Østergaard,Fabien Fritz,Signe Sofie Pladsbjerg Andresen,Karl Anker Jørgensen\",\"doi\":\"10.1021/acs.orglett.5c01444\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Halogenated maleimides can undergo either a [4 + 2] cycloaddition or a [4 + 2]/SN2 cascade reaction in an enantioselective and divergent fashion with catalytically formed trienamines. Under mild acidic conditions, [4 + 2] cycloadducts are isolated in good yields with complete diastereoselectivity and high enantioselectivity. With the addition of silver(I) benzoate as a base, a [4 + 2]/SN2 cascade reaction is induced, forming tricyclic norcaranes in moderate to good yields and with excellent overall stereoselectivity. The influence of the halogen effect on the cycloaddition was investigated experimentally, revealing a minimal impact.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"58 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-05-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.5c01444\",\"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 Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c01444","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

卤化马来酰亚胺可以与催化形成的三胺发生[4 + 2]环加成反应或[4 + 2]/SN2级联反应。在温和的酸性条件下，[4 + 2]环加合物具有完全的非对映选择性和高的对映选择性。以苯甲酸银(I)为底物，诱导了[4 + 2]/SN2级联反应，生成了产率中高的三环去甲萘烷，具有优异的整体立体选择性。实验研究了卤素效应对环加成反应的影响，结果表明卤素效应对环加成反应的影响很小。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Enantioselective and Divergent Trienamine-Mediated Reactions of Halogenated Maleimides.

Halogenated maleimides can undergo either a [4 + 2] cycloaddition or a [4 + 2]/SN2 cascade reaction in an enantioselective and divergent fashion with catalytically formed trienamines. Under mild acidic conditions, [4 + 2] cycloadducts are isolated in good yields with complete diastereoselectivity and high enantioselectivity. With the addition of silver(I) benzoate as a base, a [4 + 2]/SN2 cascade reaction is induced, forming tricyclic norcaranes in moderate to good yields and with excellent overall stereoselectivity. The influence of the halogen effect on the cycloaddition was investigated experimentally, revealing a minimal impact.

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 Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.