通过束缚反离子定向催化策略，对映选择性Au（i）催化2-炔基烯酮和萘酚之间的串联反应†

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI:10.1039/d3qo00415e

Yunliang Yu , Nazarii Sabat , Meriem Daghmoum , Zhenhao Zhang , Pascal Retailleau , Gilles Frison , Angela Marinetti , Xavier Guinchard

{"title":"通过束缚反离子定向催化策略，对映选择性Au（i）催化2-炔基烯酮和萘酚之间的串联反应†","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":"{\"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}","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

摘要

根据束缚反离子定向催化（TCDC）策略，使用具有膦-磷酸手性配体的金（i）催化剂研究了2-烷基烯酮与1-和2-萘酚的对映选择性串联环异构化/加成反应。反应在没有银添加剂的低催化剂负载量（0.2–1 mol%）下发生，萘酚同时作为O-和C-亲核试剂，产生具有高对映选择性的相应加成产物。DFT计算启发了这些过程。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy†

查看原文本刊更多论文

Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy†

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.

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

Organic chemistry frontiers : an international journal of organic chemistry

CiteScore

7.80

自引率

0.00%

发文量