钯催化菌株使[2π + 2σ]乙烯基双环[1.1.0]丁烷与亚甲基吲哚酮的环加成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-26 DOI:10.1021/acs.orglett.4c04224

Lan Zheng, Yu-Min Yang, Zhi-Ping Liu, Wei Wang, Wen-Jie Liang, Hai-Lian Jiang, Liu Yang, Chenxiang Lin, Wei Su, Jun-An Xiao

{"title":"钯催化菌株使[2π + 2σ]乙烯基双环[1.1.0]丁烷与亚甲基吲哚酮的环加成","authors":"Lan Zheng, Yu-Min Yang, Zhi-Ping Liu, Wei Wang, Wen-Jie Liang, Hai-Lian Jiang, Liu Yang, Chenxiang Lin, Wei Su, Jun-An Xiao","doi":"10.1021/acs.orglett.4c04224","DOIUrl":null,"url":null,"abstract":"A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed. The reaction enables the construction of spirobicyclo[2.1.1]hexanes bearing an all-carbon quaternary center in moderate to good yields with excellent diastereoselectivities. This method features a broad substrate scope with good functional group compatibility. The practical utility of this protocol was further demonstrated by gram-scale synthesis and postsynthetic transformations of desired product.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"32 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones\",\"authors\":\"Lan Zheng, Yu-Min Yang, Zhi-Ping Liu, Wei Wang, Wen-Jie Liang, Hai-Lian Jiang, Liu Yang, Chenxiang Lin, Wei Su, Jun-An Xiao\",\"doi\":\"10.1021/acs.orglett.4c04224\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed. The reaction enables the construction of spirobicyclo[2.1.1]hexanes bearing an all-carbon quaternary center in moderate to good yields with excellent diastereoselectivities. This method features a broad substrate scope with good functional group compatibility. The practical utility of this protocol was further demonstrated by gram-scale synthesis and postsynthetic transformations of desired product.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"32 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2024-12-26\",\"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.4c04224\",\"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.4c04224","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

研究了钯催化的乙烯基双环[1.1.0]丁烷与亚甲基吲哚酮的[2π + 2σ]环加成反应。该反应可构造具有全碳四元中心的螺环[2.1.1]己烷，产率中等至较高，具有优异的非对映选择性。该方法具有底物范围广、官能团相容性好等特点。通过克级合成和所需产物的合成后转化，进一步证明了该方案的实用性。

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

Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones

A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed. The reaction enables the construction of spirobicyclo[2.1.1]hexanes bearing an all-carbon quaternary center in moderate to good yields with excellent diastereoselectivities. This method features a broad substrate scope with good functional group compatibility. The practical utility of this protocol was further demonstrated by gram-scale synthesis and postsynthetic transformations of desired product.

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.