铜催化Si-C键裂解对映选择性合成硅立体硅二氢呋喃

IF 6.5 1区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Catalysis Pub Date : 2025-03-20 DOI:10.1016/j.jcat.2025.116089

Chuang-Chuang Su , Yong-Shun Wu , Pan-Pan Chen , An-Jiu Wen , Zheng Xu , Fei Ye , Jian Cao , Li-Wen Xu

{"title":"铜催化Si-C键裂解对映选择性合成硅立体硅二氢呋喃","authors":"Chuang-Chuang Su , Yong-Shun Wu , Pan-Pan Chen , An-Jiu Wen , Zheng Xu , Fei Ye , Jian Cao , Li-Wen Xu","doi":"10.1016/j.jcat.2025.116089","DOIUrl":null,"url":null,"abstract":"<div><div>An enantioselective synthesis of silicon-stereogenic siladihydrofuran has been developed. The key for this protocol is Cu-catalyzed Si-C bond cleavage and Si-O bond formation. In addition, catalytic hydrogenation of chiral siladihydrofuran provides carbon- and silicon-stereogenic silatetrahydrofuran in good yields with high diastereoselectivity and enantioselectivity. Ring-opening reactions of silicon-stereogenic siladihydrofuran with organolithium reagents afford enantioenriched functionalized vinylsilanes.</div></div>","PeriodicalId":346,"journal":{"name":"Journal of Catalysis","volume":"446 ","pages":"Article 116089"},"PeriodicalIF":6.5000,"publicationDate":"2025-03-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Enantioselective synthesis of silicon-stereogenic siladihydrofuran via copper-catalyzed Si-C bond cleavage\",\"authors\":\"Chuang-Chuang Su , Yong-Shun Wu , Pan-Pan Chen , An-Jiu Wen , Zheng Xu , Fei Ye , Jian Cao , Li-Wen Xu\",\"doi\":\"10.1016/j.jcat.2025.116089\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An enantioselective synthesis of silicon-stereogenic siladihydrofuran has been developed. The key for this protocol is Cu-catalyzed Si-C bond cleavage and Si-O bond formation. In addition, catalytic hydrogenation of chiral siladihydrofuran provides carbon- and silicon-stereogenic silatetrahydrofuran in good yields with high diastereoselectivity and enantioselectivity. Ring-opening reactions of silicon-stereogenic siladihydrofuran with organolithium reagents afford enantioenriched functionalized vinylsilanes.</div></div>\",\"PeriodicalId\":346,\"journal\":{\"name\":\"Journal of Catalysis\",\"volume\":\"446 \",\"pages\":\"Article 116089\"},\"PeriodicalIF\":6.5000,\"publicationDate\":\"2025-03-20\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S002195172500154X\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S002195172500154X","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

摘要

研究了一种对映选择性合成硅立体基硅二氢呋喃的方法。该方案的关键是cu催化的Si-C键裂解和Si-O键形成。此外，手性硅二氢呋喃的催化加氢反应可以得到碳和硅立体硅四氢呋喃，产率高，具有高的非对映选择性和对映选择性。硅立体基硅二氢呋喃与有机锂试剂的开环反应可得到富集对映体的功能化乙烯基硅烷。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective synthesis of silicon-stereogenic siladihydrofuran via copper-catalyzed Si-C bond cleavage

查看原文本刊更多论文

Enantioselective synthesis of silicon-stereogenic siladihydrofuran via copper-catalyzed Si-C bond cleavage

An enantioselective synthesis of silicon-stereogenic siladihydrofuran has been developed. The key for this protocol is Cu-catalyzed Si-C bond cleavage and Si-O bond formation. In addition, catalytic hydrogenation of chiral siladihydrofuran provides carbon- and silicon-stereogenic silatetrahydrofuran in good yields with high diastereoselectivity and enantioselectivity. Ring-opening reactions of silicon-stereogenic siladihydrofuran with organolithium reagents afford enantioenriched functionalized vinylsilanes.

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

Journal of Catalysis 工程技术-工程：化工

CiteScore

12.30

自引率

5.50%

发文量

447

审稿时长

31 days

期刊介绍： The Journal of Catalysis publishes scholarly articles on both heterogeneous and homogeneous catalysis, covering a wide range of chemical transformations. These include various types of catalysis, such as those mediated by photons, plasmons, and electrons. The focus of the studies is to understand the relationship between catalytic function and the underlying chemical properties of surfaces and metal complexes. The articles in the journal offer innovative concepts and explore the synthesis and kinetics of inorganic solids and homogeneous complexes. Furthermore, they discuss spectroscopic techniques for characterizing catalysts, investigate the interaction of probes and reacting species with catalysts, and employ theoretical methods. The research presented in the journal should have direct relevance to the field of catalytic processes, addressing either fundamental aspects or applications of catalysis.