{"title":"Copper-catalyzed enantioselective propargylic [3 + 2] cycloaddition: access to oxygen heterocycles featuring a CF<sub>3</sub>-substituted quaternary stereocenter.","authors":"Shweta Rohilla, Zahid Ahmad Khan, Vinod K Singh","doi":"10.1039/d4ob02043j","DOIUrl":null,"url":null,"abstract":"<p><p>A Cu(I)-Pybox-diPh catalyzed enantioselective [3 + 2] cycloaddition reaction of CF<sub>3</sub>-substituted tertiary propargylic esters as C2-bis-electrophiles with cyclic 1,3-dicarbonyl compounds as C,O-bis-nucleophiles has been reported. The methodology furnishes a variety of optically active oxygen heterocycles containing a CF<sub>3</sub>-substituted quaternary stereocenter in good yields and enantioselectivities. Moreover, the scalability of the reaction and transformations of chiral compounds into their derivatives demonstrated the synthetic and practical relevance of the approach.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob02043j","RegionNum":3,"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
Abstract
A Cu(I)-Pybox-diPh catalyzed enantioselective [3 + 2] cycloaddition reaction of CF3-substituted tertiary propargylic esters as C2-bis-electrophiles with cyclic 1,3-dicarbonyl compounds as C,O-bis-nucleophiles has been reported. The methodology furnishes a variety of optically active oxygen heterocycles containing a CF3-substituted quaternary stereocenter in good yields and enantioselectivities. Moreover, the scalability of the reaction and transformations of chiral compounds into their derivatives demonstrated the synthetic and practical relevance of the approach.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.