Asymmetric Organocatalytic Synthesis of Chiral Polycyclic 1,4‐Dihydropyridines and Axially Chiral 4‐Arylpyridines Using 2,3‐Dioxopyrrolidines and 1,3‐Diketones

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-03-21 DOI:10.1002/ejoc.202500205

Cheng-Yu Ou, Bo-Wei Huang, Ting-Hung Chu, Po-Heng Lin, Jeng-Liang Han

引用次数: 0

Abstract

An asymmetric Michael/hemiketalization/amination process of 1,3‐diketones with 2,3‐dioxopyrrolidines catalysed by a quinine‐derived urea catalyst has been developed, which furnished a series of chiral polycyclic 1,4‐dihydropyridines in satisfactory yields and enantioselectivities (35‐94% yields for 2 steps and up to 99% ee). Moreover, the subsequent oxidative aromatization of chiral 1,4‐dihydropyridines delivers the chiral atropisomeric 4‐arylpyridines in 69‐94% yields and up to 95% ee.

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在一种源于奎宁的脲催化剂催化下，开发出了一种 1,3-二酮与 2,3-二氧代吡咯烷的不对称迈克尔/半金属化/氨基化工艺，该工艺以令人满意的产率和对映选择性（2 个步骤的产率为 35-94%，ee 值高达 99%）制备出了一系列手性多环 1,4-二氢吡啶。此外，手性 1,4-二氢吡啶的后续氧化芳香化反应可得到手性异构的 4-芳基吡啶，收率为 69-94%，ee 值高达 95%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.