Sufang Shao, Yuan Yang, Alban Schmoll, Xiao-Feng Wu
{"title":"Copper-Catalyzed Asymmetric Carbonylative Hydroallylation of Vinylarenes","authors":"Sufang Shao, Yuan Yang, Alban Schmoll, Xiao-Feng Wu","doi":"10.1039/d5sc02421h","DOIUrl":null,"url":null,"abstract":"We describe a novel and efficient copper-catalyzed carbonylative hydroallylation of vinylarenes, providing a direct route to chiral α,β-unsaturated ketones, which are important compounds in organic synthesis and bioactive molecules. The method employs readily accessible vinylarenes and allylic phosphates, utilizing carbon monoxide as the carbonyl source under mild reaction conditions. The reaction demonstrates a broad substrate scope, including diverse vinylarenes with various functional groups, as well as vinylarenes derived from natural products. Additionally, all four stereoisomers of a chiral allylic alcohol were prepared by employing this strategy, showcasing its versatility in stereodivergent synthesis.","PeriodicalId":9909,"journal":{"name":"Chemical Science","volume":"52 1","pages":""},"PeriodicalIF":7.6000,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Science","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5sc02421h","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
We describe a novel and efficient copper-catalyzed carbonylative hydroallylation of vinylarenes, providing a direct route to chiral α,β-unsaturated ketones, which are important compounds in organic synthesis and bioactive molecules. The method employs readily accessible vinylarenes and allylic phosphates, utilizing carbon monoxide as the carbonyl source under mild reaction conditions. The reaction demonstrates a broad substrate scope, including diverse vinylarenes with various functional groups, as well as vinylarenes derived from natural products. Additionally, all four stereoisomers of a chiral allylic alcohol were prepared by employing this strategy, showcasing its versatility in stereodivergent synthesis.
期刊介绍:
Chemical Science is a journal that encompasses various disciplines within the chemical sciences. Its scope includes publishing ground-breaking research with significant implications for its respective field, as well as appealing to a wider audience in related areas. To be considered for publication, articles must showcase innovative and original advances in their field of study and be presented in a manner that is understandable to scientists from diverse backgrounds. However, the journal generally does not publish highly specialized research.