{"title":"相转移催化的芳基乙酸酯的对映选择性 α-烷基化反应","authors":"Yinuo Xiao, Zhenpeng Li, Changming Xu","doi":"10.1016/j.tetlet.2024.155347","DOIUrl":null,"url":null,"abstract":"<div><div>A chiral spirocyclic quaternary ammonium salt catalyzed asymmetric alkylation, especially methylation, of α-aryl esters possessing inherently poor reactivity under strong basic conditions has been developed, giving the target products with up to 94 % ee. This mild process was also applied to synthesize optically pure naproxen.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"152 ","pages":"Article 155347"},"PeriodicalIF":1.5000,"publicationDate":"2024-11-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates\",\"authors\":\"Yinuo Xiao, Zhenpeng Li, Changming Xu\",\"doi\":\"10.1016/j.tetlet.2024.155347\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A chiral spirocyclic quaternary ammonium salt catalyzed asymmetric alkylation, especially methylation, of α-aryl esters possessing inherently poor reactivity under strong basic conditions has been developed, giving the target products with up to 94 % ee. This mild process was also applied to synthesize optically pure naproxen.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"152 \",\"pages\":\"Article 155347\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-11-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924004428\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/10/28 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004428","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/10/28 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
我们开发了一种手性螺环季铵盐催化的不对称烷基化（尤其是甲基化）α-芳基酯的方法，这种酯在强碱性条件下固有的反应性很差，但却能得到高达 94 % ee 的目标产物。这种温和的工艺还被用于合成光学纯萘普生。
Phase-transfer-catalyzed enantioselective α-alkylation of aryl acetates
A chiral spirocyclic quaternary ammonium salt catalyzed asymmetric alkylation, especially methylation, of α-aryl esters possessing inherently poor reactivity under strong basic conditions has been developed, giving the target products with up to 94 % ee. This mild process was also applied to synthesize optically pure naproxen.
期刊介绍：
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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