{"title":"Enantioselective Vinylogous Addition of Enones to Allenes Enabled by Synergistic Borane/Palladium Catalysis","authors":"Heng Luo, Ming Zhang, Ze-Qun Xing, Xiao-Chen Wang","doi":"10.1021/jacs.4c16214","DOIUrl":null,"url":null,"abstract":"Herein, we report a method for enantioselective vinylogous addition of enones to alkoxyallenes enabled by synergistic borane/palladium catalysis. The inductive effect provided by borane coordination to the ketone was essential for closing the gap between the conditions needed for the generation of a dienolate and those needed for initiation of the palladium catalytic cycle by protonation of the metal catalyst. Furthermore, we accomplished the first example of stereodivergent synthesis with chiral borane/transition-metal catalysts.","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":"185 1","pages":""},"PeriodicalIF":14.4000,"publicationDate":"2024-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/jacs.4c16214","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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Abstract
Herein, we report a method for enantioselective vinylogous addition of enones to alkoxyallenes enabled by synergistic borane/palladium catalysis. The inductive effect provided by borane coordination to the ketone was essential for closing the gap between the conditions needed for the generation of a dienolate and those needed for initiation of the palladium catalytic cycle by protonation of the metal catalyst. Furthermore, we accomplished the first example of stereodivergent synthesis with chiral borane/transition-metal catalysts.
期刊介绍：
The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.
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