Jing-Liang Yu , Su-Fan Gao , Chun-Jun Zhu , Wen-Sheng Li , Li-Xin Wang
{"title":"一种奎宁方酰胺催化的对映体选择性[4 + 2]环加成反应，用于制备手性 3, 4-二氢香豆素的邻羟基苯基对苯醌甲醚和γ-丁烯酸酯","authors":"Jing-Liang Yu , Su-Fan Gao , Chun-Jun Zhu , Wen-Sheng Li , Li-Xin Wang","doi":"10.1016/j.tetlet.2024.155311","DOIUrl":null,"url":null,"abstract":"<div><div>A quinine-squaramide catalyzed enantioselective inverse-electron-demand hetero-Diels–Alder reaction between γ-butenolides and <em>ortho</em>-hydroxyphenyl <em>p</em>-QMs has been disclosed. A wide range of chiral 3, 4-dihydrocoumarins frameworks with two adjacent stereogenic centers have been directly and concisely prepared in excellent results (up to 94 % yield, 99:1 dr, 98:2 er) under mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"151 ","pages":"Article 155311"},"PeriodicalIF":1.5000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A quinine squaramide catalyzed enantioselective [4 + 2] cycloaddition between ortho-hydroxyphenyl para-quinone methide and γ-butenolides for preparation of chiral 3, 4-dihydrocoumarins\",\"authors\":\"Jing-Liang Yu , Su-Fan Gao , Chun-Jun Zhu , Wen-Sheng Li , Li-Xin Wang\",\"doi\":\"10.1016/j.tetlet.2024.155311\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A quinine-squaramide catalyzed enantioselective inverse-electron-demand hetero-Diels–Alder reaction between γ-butenolides and <em>ortho</em>-hydroxyphenyl <em>p</em>-QMs has been disclosed. A wide range of chiral 3, 4-dihydrocoumarins frameworks with two adjacent stereogenic centers have been directly and concisely prepared in excellent results (up to 94 % yield, 99:1 dr, 98:2 er) under mild conditions.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"151 \",\"pages\":\"Article 155311\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-11-13\",\"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/S0040403924004064\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/9/25 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/S0040403924004064","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/25 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
A quinine squaramide catalyzed enantioselective [4 + 2] cycloaddition between ortho-hydroxyphenyl para-quinone methide and γ-butenolides for preparation of chiral 3, 4-dihydrocoumarins
A quinine-squaramide catalyzed enantioselective inverse-electron-demand hetero-Diels–Alder reaction between γ-butenolides and ortho-hydroxyphenyl p-QMs has been disclosed. A wide range of chiral 3, 4-dihydrocoumarins frameworks with two adjacent stereogenic centers have been directly and concisely prepared in excellent results (up to 94 % yield, 99:1 dr, 98:2 er) under mild conditions.
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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