{"title":"Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy†","authors":"Yunliang Yu , Nazarii Sabat , Meriem Daghmoum , Zhenhao Zhang , Pascal Retailleau , Gilles Frison , Angela Marinetti , Xavier Guinchard","doi":"10.1039/d3qo00415e","DOIUrl":null,"url":null,"abstract":"<div><p>Enantioselective tandem cycloisomerization/addition reactions of 2-alkynyl enones with 1- and 2-naphthols have been investigated using gold(<span>i</span>) catalysts featuring hybrid phosphine–phosphoric acid chiral ligands, according to the tethered counterion-directed catalysis (TCDC) strategy. The reactions occur at low catalyst loading (0.2–1 mol%) without silver additives, and the naphthols act as both <em>O</em>- and <em>C</em>-nucleophiles, leading to the corresponding addition products with high enantioselectivity. DFT calculations enlighten these processes.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 12","pages":"Pages 2936-2942"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023008295","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Enantioselective tandem cycloisomerization/addition reactions of 2-alkynyl enones with 1- and 2-naphthols have been investigated using gold(i) catalysts featuring hybrid phosphine–phosphoric acid chiral ligands, according to the tethered counterion-directed catalysis (TCDC) strategy. The reactions occur at low catalyst loading (0.2–1 mol%) without silver additives, and the naphthols act as both O- and C-nucleophiles, leading to the corresponding addition products with high enantioselectivity. DFT calculations enlighten these processes.
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