喹啉的逐步脱芳化/硝化/对映选择性同烯酸酯反应生成c3 -硝基取代四氢喹啉。

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-03-18 DOI:10.1039/D5OB00247H

Aniruddh Pratap and Biswajit Maji

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引用次数: 0

摘要

在此，我们描述了喹啉的逐步1,2-还原脱芳/选择性c3 -硝化和随后的催化对映选择性齐烯酸酯加成反应，使用NHC催化剂策略构建n -乙酰3,4-二取代四氢喹啉，收率高，具有非常高的非映和对映选择性（dr bbb99: 1， ee高达>99%）。本文还实现了一种以易得的喹啉为原料合成3-硝基喹啉的高效无金属无碱方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A stepwise dearomatization/nitration/enantioselective homoenolate reaction of quinolines to construct C3-nitro-substituted tetrahydroquinolines†

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A stepwise dearomatization/nitration/enantioselective homoenolate reaction of quinolines to construct C3-nitro-substituted tetrahydroquinolines†

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.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

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.