金（I）催化的从 1-硅烷化炔烃获得 1-炔基 C-糖苷的途径：糖苷的直接和 α-全选择性炔化的另一种范式

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL ACS Catalysis Pub Date : 2024-09-23 DOI:10.1021/acscatal.4c04293

Eliot Starck, Mathieu Pascaretti, Catherine Taillier, Aurélien Blanc, Vincent Dalla, Patrick Pale, Jean-Marc Weibel

{"title":"金（I）催化的从 1-硅烷化炔烃获得 1-炔基 C-糖苷的途径：糖苷的直接和 α-全选择性炔化的另一种范式","authors":"Eliot Starck, Mathieu Pascaretti, Catherine Taillier, Aurélien Blanc, Vincent Dalla, Patrick Pale, Jean-Marc Weibel","doi":"10.1021/acscatal.4c04293","DOIUrl":null,"url":null,"abstract":"Analogous to O-glycosides, C-glycosides are natural products exhibiting various bioactivities. Alkynyl C-glycosides represent important key intermediates toward more complex derivatives; however, a convenient access through a single catalytic and highly stereocontrolled step remains an important and only partially solved challenge. Here, a mechanistically designed gold(I)-catalyzed silyl-assisted efficient and highly α-stereoselective process is reported. The postulated mechanism has been ascertained by combining 1H, 31P and VT NMR and in situ MS experiments.","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":null,"pages":null},"PeriodicalIF":11.3000,"publicationDate":"2024-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Gold(I)-Catalyzed Access to 1-Alkynyl C-Glycosides from 1-Silylated Alkynes: An Alternative Paradigm for the Direct and α-Stereoselective Alkynylation of Glycosides\",\"authors\":\"Eliot Starck, Mathieu Pascaretti, Catherine Taillier, Aurélien Blanc, Vincent Dalla, Patrick Pale, Jean-Marc Weibel\",\"doi\":\"10.1021/acscatal.4c04293\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Analogous to O-glycosides, C-glycosides are natural products exhibiting various bioactivities. Alkynyl C-glycosides represent important key intermediates toward more complex derivatives; however, a convenient access through a single catalytic and highly stereocontrolled step remains an important and only partially solved challenge. Here, a mechanistically designed gold(I)-catalyzed silyl-assisted efficient and highly α-stereoselective process is reported. The postulated mechanism has been ascertained by combining 1H, 31P and VT NMR and in situ MS experiments.\",\"PeriodicalId\":9,\"journal\":{\"name\":\"ACS Catalysis \",\"volume\":null,\"pages\":null},\"PeriodicalIF\":11.3000,\"publicationDate\":\"2024-09-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Catalysis \",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acscatal.4c04293\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acscatal.4c04293","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

摘要

与 O 型糖苷类似，C 型糖苷也是具有各种生物活性的天然产物。炔基 C-糖苷是通向更复杂衍生物的重要关键中间体；然而，如何通过单一催化和高度立体可控的步骤方便地获得 C-糖苷仍然是一个重要的挑战，而且只得到了部分解决。本文报告了一种从机制上设计的金(I)催化硅烷辅助的高效、高α-立体选择性过程。通过结合 1H、31P 和 VT NMR 以及原位 MS 实验，确定了推测的机理。

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

微信好友朋友圈 QQ好友复制链接

本刊更多论文

Gold(I)-Catalyzed Access to 1-Alkynyl C-Glycosides from 1-Silylated Alkynes: An Alternative Paradigm for the Direct and α-Stereoselective Alkynylation of Glycosides

Analogous to O-glycosides, C-glycosides are natural products exhibiting various bioactivities. Alkynyl C-glycosides represent important key intermediates toward more complex derivatives; however, a convenient access through a single catalytic and highly stereocontrolled step remains an important and only partially solved challenge. Here, a mechanistically designed gold(I)-catalyzed silyl-assisted efficient and highly α-stereoselective process is reported. The postulated mechanism has been ascertained by combining ¹H, ³¹P and VT NMR and in situ MS experiments.

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

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.