Olga V. Turova, Albert G. Nigmatov, Evgeniya V. Filatova, Andrei A. Vasil’ev, Sergei G. Zlotin
{"title":"在二氧化碳介质中有机催化形成 (3R,3aS,9bR)-构型 3-芳基-3a-苯甲酰胺基-1,3a,4,9b-四氢苯并吡喃并[4,3-b]吡咯的多米诺效应","authors":"Olga V. Turova, Albert G. Nigmatov, Evgeniya V. Filatova, Andrei A. Vasil’ev, Sergei G. Zlotin","doi":"10.1016/j.mencom.2024.09.022","DOIUrl":null,"url":null,"abstract":"<div><div>Asymmetric cycloaddition/intramolecular rearrangement domino reaction of 2-(2-hydroxybenzylideneamino)- malonates with 4-arylidene-2-phenyloxazol-5(4<em>H</em>)-ones can be efficiently carried out in sub- or supercritical carbon dioxide to afford (3<em>R</em>,3a<em>S</em>,9b<em>R</em>)-3-aryl-3a-benzamido-4-oxo-1,3a,4,9b-tetrahydrochromeno[4,3-<em>b</em>]pyrrole-2,2(3<em>H</em>)- dicarboxylates in high yields with up to 99% <em>ee</em>. Excellent stereoinduction is provided in this process by the use of bifunctional hybrid organocatalyst consisting of squaramide (thiourea) and chiral tertiary amine units.</div></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":"34 5","pages":"Pages 694-697"},"PeriodicalIF":1.8000,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium\",\"authors\":\"Olga V. Turova, Albert G. Nigmatov, Evgeniya V. Filatova, Andrei A. Vasil’ev, Sergei G. Zlotin\",\"doi\":\"10.1016/j.mencom.2024.09.022\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Asymmetric cycloaddition/intramolecular rearrangement domino reaction of 2-(2-hydroxybenzylideneamino)- malonates with 4-arylidene-2-phenyloxazol-5(4<em>H</em>)-ones can be efficiently carried out in sub- or supercritical carbon dioxide to afford (3<em>R</em>,3a<em>S</em>,9b<em>R</em>)-3-aryl-3a-benzamido-4-oxo-1,3a,4,9b-tetrahydrochromeno[4,3-<em>b</em>]pyrrole-2,2(3<em>H</em>)- dicarboxylates in high yields with up to 99% <em>ee</em>. Excellent stereoinduction is provided in this process by the use of bifunctional hybrid organocatalyst consisting of squaramide (thiourea) and chiral tertiary amine units.</div></div>\",\"PeriodicalId\":18542,\"journal\":{\"name\":\"Mendeleev Communications\",\"volume\":\"34 5\",\"pages\":\"Pages 694-697\"},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-09-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Mendeleev Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S095994362400261X\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Mendeleev Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S095994362400261X","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium
Asymmetric cycloaddition/intramolecular rearrangement domino reaction of 2-(2-hydroxybenzylideneamino)- malonates with 4-arylidene-2-phenyloxazol-5(4H)-ones can be efficiently carried out in sub- or supercritical carbon dioxide to afford (3R,3aS,9bR)-3-aryl-3a-benzamido-4-oxo-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrrole-2,2(3H)- dicarboxylates in high yields with up to 99% ee. Excellent stereoinduction is provided in this process by the use of bifunctional hybrid organocatalyst consisting of squaramide (thiourea) and chiral tertiary amine units.
期刊介绍：
Mendeleev Communications is the journal of the Russian Academy of Sciences, launched jointly by the Academy of Sciences of the USSR and the Royal Society of Chemistry (United Kingdom) in 1991. Starting from 1st January 2007, Elsevier is the new publishing partner of Mendeleev Communications.
Mendeleev Communications publishes short communications in chemistry. The journal primarily features papers from the Russian Federation and the other states of the former USSR. However, it also includes papers by authors from other parts of the world. Mendeleev Communications is not a translated journal, but instead is published directly in English. The International Editorial Board is composed of eminent scientists who provide advice on refereeing policy.
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