{"title":"From gem-Dichlorocyclobutenones to Cyclobutenols: Unveiling a Ruthenium-Catalyzed Allylic Reduction-Asymmetric Transfer Hydrogenation Cascade","authors":"Christophe MEYER, Olivier Charron, Marharyta Kosiuha, Virginie Ratovelomanana-Vidal, Phannarath Phansavath, Geoffrey Gontard","doi":"10.1002/adsc.202401406","DOIUrl":null,"url":null,"abstract":"Cyclobutenones constitute an appealing class of substrates in catalytic asymmetric transformations leading to diversely substituted enantioenriched four-membered carbocycles, which are eliciting a growing interest in medicinal chemistry. Whilst several synthetically useful enantioselective conjugate addition reactions have been reported, the catalytic enantioselective reduction of the carbonyl group of simple cyclobutenones remains an elusive transformation. Herein, we disclose the discovery of a novel allylic reduction-asymmetric transfer hydrogenation cascade, catalyzed by a Noyori-Ikariya ruthenium complex, from readily available gem-dichlorocyclobutenones, leading to 2-chlorocyclobutenols with high optical purities, which can be engaged in postfunctionalization reactions enabling access to substituted four-membered rings.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"9 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401406","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
Cyclobutenones constitute an appealing class of substrates in catalytic asymmetric transformations leading to diversely substituted enantioenriched four-membered carbocycles, which are eliciting a growing interest in medicinal chemistry. Whilst several synthetically useful enantioselective conjugate addition reactions have been reported, the catalytic enantioselective reduction of the carbonyl group of simple cyclobutenones remains an elusive transformation. Herein, we disclose the discovery of a novel allylic reduction-asymmetric transfer hydrogenation cascade, catalyzed by a Noyori-Ikariya ruthenium complex, from readily available gem-dichlorocyclobutenones, leading to 2-chlorocyclobutenols with high optical purities, which can be engaged in postfunctionalization reactions enabling access to substituted four-membered rings.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.