{"title":"A stepwise dearomatization/nitration/enantioselective homoenolate reaction of quinolines to construct C3-nitro-substituted tetrahydroquinolines†","authors":"Aniruddh Pratap , Biswajit Maji","doi":"10.1039/d5ob00247h","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we describe a stepwise 1,2-reductive dearomatization/selective C<sub>3</sub>-nitration of quinoline and a subsequent catalytic enantioselective homoenolate addition reaction using a NHC catalyst strategy to construct <em>N</em>-acetyl 3,4-disubstituted tetrahydroquinoline in good yields with remarkably high diastereo- and enantioselectivities (dr >99 : 1, ee up to >99%). An efficient metal- and base-free method for 3-nitroquinoline synthesis from readily accessible quinoline has also been realized.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 16","pages":"Pages 3812-3818"},"PeriodicalIF":2.7000,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025002216","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/3/18 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we describe a stepwise 1,2-reductive dearomatization/selective C3-nitration of quinoline and a subsequent catalytic enantioselective homoenolate addition reaction using a NHC catalyst strategy to construct N-acetyl 3,4-disubstituted tetrahydroquinoline in good yields with remarkably high diastereo- and enantioselectivities (dr >99 : 1, ee up to >99%). An efficient metal- and base-free method for 3-nitroquinoline synthesis from readily accessible quinoline has also been realized.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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