Enantioselective Organophotocatalytic α-Functionalization of Aldehydes with N-Lactam Radicals: A Viable Strategy for the Telescoped Synthesis of Levetiracetam.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-29 DOI:10.1021/acs.orglett.5c02365

Eleonora Colombo,Monica Fiorenza Boselli,Marco Fattalini,Valerio Chiroli,Sergio Rossi,Maurizio Benaglia,Alessandra Puglisi

引用次数: 0

Abstract

The mild photocatalytic generation of N-lactam radicals is explored for the enantioselective α-functionalization of aldehydes in the presence of a chiral imidazolidinone organocatalyst. The reaction provides the desired products in high yields and up to 92% ee using a structurally simple, low-cost, and easy-to-prepare organocatalyst. The methodology was successfully applied to the telescoped synthesis of a pharmacologically relevant compound, (S)-levetiracetam, an antiepileptic drug.

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n -内酰胺自由基α-功能化醛的对映选择性有机光催化：伸缩合成左乙拉西坦的可行策略。

在手性咪唑烷酮有机催化剂的存在下，探讨了n -内酰胺自由基的温和光催化生成对映选择性α-功能化醛。该反应采用结构简单、成本低、易于制备的有机催化剂，产率高，ee达92%。该方法成功地应用于抗癫痫药物(S)-左乙拉西坦的缩合合成。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.