An Efficient Asymmetric Synthesis of Finerenone via Evans' Chiral Auxiliary

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-06-10 DOI:10.1002/ejoc.202500538

Safomuddin Abduahadi, Emmanuel Mintah Bonku, Fuqiang Zhu, Feipu Yang, Samuel Desta Guma, Zayniddin Nuriddinov, Hongjian Qin, Jingshan Shen

引用次数: 0

Abstract

This article reports a new application of Evans' chiral auxiliary for an efficient asymmetric synthesis of finerenone. This new application successfully achieves the key step of stereoselective construction of the naphthyridine core of finerenone, with a high diastereomeric ratio (dr 86:14) and an 80% yield of the desired product via Evans’ chiral (R)-4-benzyl-2-oxazolidinone. The downstream transamidation of ethyl ester, with ammonia, leads to the formation of finerenone.

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利用Evans手性助剂高效非对称合成芬烯酮

本文报道了Evans手性助剂在精细烯酮不对称合成中的新应用。这一新的应用成功地实现了细烯酮的萘啶核立体选择性构建的关键步骤，具有很高的非对映比（dr 86:14），并且通过Evans的手性(R)-4-苄基-2-恶唑烷酮得到所需产物的收率为80%。乙酯与氨的下游转氨化反应生成细烯酮。

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.