二乙基氯化铝介导的亚胺取代降冰片烯的环加成/共轭还原序列

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI:10.1002/ejoc.202401270

Manuel Kirchhof , Derman Batman , Elliot Nicholas , Wolfgang Frey , Volker Derdau , Anna Zens , Sabine Laschat

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引用次数: 0

摘要

二乙基氯化铝是一种已知的路易斯酸，可以进行1,2-和1,4-加成，而共轭还原主要是副反应。我们偶然发现了一个由et2alcl促进的环戊二烯和4-异丙基-3-（3-苯基丙基）恶唑烷-2- 1的顺序环加成/共轭加氢反应，从而得到相应的降冰片烯-恶唑烷-2- 1。核磁共振、动力学和氘化实验为该反应序列的机理提供了新的思路。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Diethylaluminium Chloride‐Mediated Cycloaddition/Conjugate Reduction Sequence towards Imido‐Substituted Norbornenes

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Diethylaluminium Chloride‐Mediated Cycloaddition/Conjugate Reduction Sequence towards Imido‐Substituted Norbornenes

Diethylaluminium chloride is a known Lewis acid and can undergo 1,2‐ and 1,4‐additions, whereas conjugate reductions are mostly observed as side reactions. By serendipity we found a Et₂AlCl‐promoted sequential cycloaddition/conjugate hydrogenation of cyclopentadiene and 4‐isopropyl‐3‐(3‐phenylpropioloyl) oxazolidin‐2‐one resulting in the clean formation of the corresponding norbornene‐oxazolidin‐2‐one. NMR, kinetic and deuteration experiments provided insight into the mechanism of this reaction sequence.

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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.