{"title":"Chemo- and Enantioselective Intermolecular Allylation of Quinolin-2-ones","authors":"Zihao Li, Yumeng Wang, Yuqiao Zhou, Zongli Xiong, Jian Wang, Weijun Yao, Zhen Wang","doi":"10.1002/adsc.202401113","DOIUrl":null,"url":null,"abstract":"An enantioselective C-, O- and N- intermolecular allylic reaction of quinolin-2(1H)-ones has been developed. The reaction between 3-hydroxy quinolone and Boc-protected MBH adducts with Pd-catalysis provided a series of 1,4-dihydroquinoline-2,3-diones in 20-95% yield accompanied by 69-96% enantioselectivity. In addition, the O-allylic alkylation could occur by varying the organo-catalyst and Boc-protected MBH adducts from benzaldehyde. Furthermore, the N-allylation of 3-O-protected quinolin-2-ones with allylic acetates was also realized (40-92% yield, 78-97% ee).","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"115 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-12-08","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.202401113","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
An enantioselective C-, O- and N- intermolecular allylic reaction of quinolin-2(1H)-ones has been developed. The reaction between 3-hydroxy quinolone and Boc-protected MBH adducts with Pd-catalysis provided a series of 1,4-dihydroquinoline-2,3-diones in 20-95% yield accompanied by 69-96% enantioselectivity. In addition, the O-allylic alkylation could occur by varying the organo-catalyst and Boc-protected MBH adducts from benzaldehyde. Furthermore, the N-allylation of 3-O-protected quinolin-2-ones with allylic acetates was also realized (40-92% yield, 78-97% ee).
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.
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