{"title":"CuH-Catalyzed Regio- and Enantioselective Hydroallylation of 1-Trifluoromethylthioalkenes: Leaving Group-Dependent Stereochemistry.","authors":"Yuki Kojima, Shinichi Suda, Wataru Kanna, Yuji Nishii, Satoshi Maeda, Koji Hirano","doi":"10.1002/chem.202501210","DOIUrl":null,"url":null,"abstract":"<p><p>A copper-catalyzed regio- and enantioselective hydroallylation of 1-trifluoromethylthioalkenes with hydrosilanes and allylic electrophiles has been developed. The judicious choice of chiral ligands successfully promotes the enantioselective C(sp3)-C(sp3) bond formation at the α-position of trifluoromethylthio (SCF3) group, which is otherwise difficult to perform by other means. Experimental and computational mechanistic studies reveal that leaving groups of allylic electrophiles significantly influence the enantioselectivity as well as chemoselectivity.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e202501210"},"PeriodicalIF":3.9000,"publicationDate":"2025-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - A European Journal","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/chem.202501210","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A copper-catalyzed regio- and enantioselective hydroallylation of 1-trifluoromethylthioalkenes with hydrosilanes and allylic electrophiles has been developed. The judicious choice of chiral ligands successfully promotes the enantioselective C(sp3)-C(sp3) bond formation at the α-position of trifluoromethylthio (SCF3) group, which is otherwise difficult to perform by other means. Experimental and computational mechanistic studies reveal that leaving groups of allylic electrophiles significantly influence the enantioselectivity as well as chemoselectivity.
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