R. N. Yadav, A. Shaikh, Aparna Das, D. Ray, B. Banik
{"title":"3-吡咯取代物的不对称合成-对甲苯磺酸催化氮杂环丁烷-2,3-二酮与羟基脯氨酸反应制备乳酸","authors":"R. N. Yadav, A. Shaikh, Aparna Das, D. Ray, B. Banik","doi":"10.2174/2213337209666220802105301","DOIUrl":null,"url":null,"abstract":"\n\nThe aim of this study is to investigate the p-toluene sulphonic acid (p-Ts.OH) catalyzed reaction of racemic-azetidine-2,3-diones with enantiomerically pure cis and trans-4-hydroxy-L-proline in refluxing ethanol culminating in a synthesis of substituted novel 3-(pyrrol-1-yl)-azetidin-2-ones at the C-3 position. This work describes an alternative synthetic route enabling the tandem transformation of proline to pyrrole, followed by intramolecular chirality transfer to the -lactams ring. All four diastereomers of 3-(pyrrol-1-yl)-azetidin-2-ones could be achieved in good to excellent yield with high diastereoselectivity in a single-pot operation.\n","PeriodicalId":10945,"journal":{"name":"Current Organocatalysis","volume":"28 1","pages":""},"PeriodicalIF":0.9000,"publicationDate":"2022-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Asymmetric Synthesis of 3-Pyrrole Substituted -Lactams Through p-Toluene sulphonic Acid-Catalyzed Reaction of azetidine-2,3-diones with Hydroxyprolines\",\"authors\":\"R. N. Yadav, A. Shaikh, Aparna Das, D. Ray, B. Banik\",\"doi\":\"10.2174/2213337209666220802105301\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"\\n\\nThe aim of this study is to investigate the p-toluene sulphonic acid (p-Ts.OH) catalyzed reaction of racemic-azetidine-2,3-diones with enantiomerically pure cis and trans-4-hydroxy-L-proline in refluxing ethanol culminating in a synthesis of substituted novel 3-(pyrrol-1-yl)-azetidin-2-ones at the C-3 position. This work describes an alternative synthetic route enabling the tandem transformation of proline to pyrrole, followed by intramolecular chirality transfer to the -lactams ring. All four diastereomers of 3-(pyrrol-1-yl)-azetidin-2-ones could be achieved in good to excellent yield with high diastereoselectivity in a single-pot operation.\\n\",\"PeriodicalId\":10945,\"journal\":{\"name\":\"Current Organocatalysis\",\"volume\":\"28 1\",\"pages\":\"\"},\"PeriodicalIF\":0.9000,\"publicationDate\":\"2022-08-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Current Organocatalysis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.2174/2213337209666220802105301\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Organocatalysis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/2213337209666220802105301","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Asymmetric Synthesis of 3-Pyrrole Substituted -Lactams Through p-Toluene sulphonic Acid-Catalyzed Reaction of azetidine-2,3-diones with Hydroxyprolines
The aim of this study is to investigate the p-toluene sulphonic acid (p-Ts.OH) catalyzed reaction of racemic-azetidine-2,3-diones with enantiomerically pure cis and trans-4-hydroxy-L-proline in refluxing ethanol culminating in a synthesis of substituted novel 3-(pyrrol-1-yl)-azetidin-2-ones at the C-3 position. This work describes an alternative synthetic route enabling the tandem transformation of proline to pyrrole, followed by intramolecular chirality transfer to the -lactams ring. All four diastereomers of 3-(pyrrol-1-yl)-azetidin-2-ones could be achieved in good to excellent yield with high diastereoselectivity in a single-pot operation.
期刊介绍：
Current Organocatalysis is an international peer-reviewed journal that publishes significant research in all areas of organocatalysis. The journal covers organo homogeneous/heterogeneous catalysis, innovative mechanistic studies and kinetics of organocatalytic processes focusing on practical, theoretical and computational aspects. It also includes potential applications of organocatalysts in the fields of drug discovery, synthesis of novel molecules, synthetic method development, green chemistry and chemoenzymatic reactions. This journal also accepts papers on methods, reagents, and mechanism of a synthetic process and technology pertaining to chemistry. Moreover, this journal features full-length/mini review articles within organocatalysis and synthetic chemistry. It is the premier source of organocatalysis and synthetic methods related information for chemists, biologists and engineers pursuing research in industry and academia.
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