Manuel Kirchhof , Derman Batman , Elliot Nicholas , Wolfgang Frey , Volker Derdau , Anna Zens , Sabine Laschat
{"title":"Diethylaluminium Chloride‐Mediated Cycloaddition/Conjugate Reduction Sequence towards Imido‐Substituted Norbornenes","authors":"Manuel Kirchhof , Derman Batman , Elliot Nicholas , Wolfgang Frey , Volker Derdau , Anna Zens , Sabine Laschat","doi":"10.1002/ejoc.202401270","DOIUrl":null,"url":null,"abstract":"<div><div>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 Et<sub>2</sub>AlCl‐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.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202401270"},"PeriodicalIF":2.5000,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202401270","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X25000763","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
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.
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.