Asymmetric synthesis of chiral 4,5,6-trisubstituted-3,4-dihydropyrimidinethiones catalyzed by chiral Brønsted acid

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2026-01-15 Epub Date: 2025-10-27 DOI:10.1016/j.tet.2025.134999

Lingkai Kong, Zhe Li, Chunzhi Ju, Peng Wang, Guangliang Zhang, Suoqin Zhang

引用次数: 0

Abstract

The low steric hindrance of small-substituent 2,4-diketones presents a significant challenge for effective asymmetric induction.An efficient and highly enantioselective catalytic system was developed for the Biginelli reaction to access chiral 4,5,6-trisubstituted-3,4-dihydropyrimidinethiones. Through catalyst screening, chiral imidodiphosphoric acid was found to outperform conventional chiral phosphoric acids. Under the optimized conditions, up to 99 % ee and 52–92 % isolated yields were achieved. This method offers a valuable strategy for the asymmetric synthesis of bioactive pyrimidine derivatives with potential pharmaceutical applicatioins.

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手性Brønsted酸催化不对称合成4,5,6-三取代-3,4-二氢嘧啶硫酮

小取代基2,4-二酮的低空间位阻对有效的不对称诱导提出了重大挑战。为获得手性4,5,6-三取代-3,4-二氢嘧啶硫酮，建立了一种高效、高对映选择性的Biginelli反应催化体系。通过催化剂筛选，发现手性咪胺二磷酸的催化性能优于常规手性磷酸。在此条件下，分离率可达52 ~ 92%，ee可达99%。该方法为不对称合成具有生物活性的嘧啶衍生物提供了一种有价值的方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.