{"title":"Nickel-Catalyzed One-Pot H/D Exchange and Asymmetric Michael Addition in the Presence of D2O","authors":"Junyu Zhou, Yuxiang Zhang, Jing Zhou, Yan Min, Haoting Wang, Jingyi Ruan, Dong Zhang, Hui Zhou, Biao Xia","doi":"10.1021/acs.joc.4c02860","DOIUrl":null,"url":null,"abstract":"A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective and readily available deuterium source is highly desirable. Herein, we report a nickel-catalyzed one-pot H/D exchange and highly enantioselective Michael addition of α,β-unsaturated 2-acyl imidazoles with nitromethane in the presence of D<sub>2</sub>O. This protocol demonstrates excellent efficiency, high enantioselectivity, and a broad substrate scope, offering a practical and versatile approach to accessing deuterium-labeled compounds.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"101 1","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c02860","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A step-economical and efficient strategy for the enantioselective synthesis of tetradeuterated γ-nitroketones using a cost-effective and readily available deuterium source is highly desirable. Herein, we report a nickel-catalyzed one-pot H/D exchange and highly enantioselective Michael addition of α,β-unsaturated 2-acyl imidazoles with nitromethane in the presence of D2O. This protocol demonstrates excellent efficiency, high enantioselectivity, and a broad substrate scope, offering a practical and versatile approach to accessing deuterium-labeled compounds.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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