Hetero diacylation of 1,1-diborylalkanes: Practical synthesis of 1,3-diketones |
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| Institution: | 1. Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Pharmaceutical Sciences, Jiangnan University, Wuxi 214122, China;2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China;1. Laboratorio de Química Inorgánica, Instituto de Química, Pontificia Universidad Católica de Valparaíso, Campus Curauma, Avenida Universidad 330, Valparaíso, Chile;2. Laboratorio de Química Orgánica 1, Instituto de Química, Pontificia Universidad Católica de Valparaíso, Campus Curauma, Avenida Universidad 330, Valparaíso, Chile;3. UMR 6226 “Institut des Sciences Chimiques de Rennes”, CNRS-Université de Rennes 1, Centre de Diffractométrie X, Campus de Beaulieu, 35042 Rennes Cedex, France;4. UMR 6226 “Institut des Sciences Chimiques de Rennes”, CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France;1. Key Laboratory of Molecular Target & Clinical Pharmacology, State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, China;2. Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China;3. Guangdong Institute of Analysis (China National Analytical Center, Guangzhou), Guangzhou 510070, China;1. Key Laboratory of Biomedical Polymers, Engineering Research Centre of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China;2. Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055, China;3. School of Pharmaceutical Sciences (Shenzhen), Sun Yat-sen University, Shenzhen 518107, China;1. Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, Glasgow G1 1XL, UK;1. Institute of Next Generation Matter Transformation, College of Chemical Engineering and College of Material Sciences Engineering, Huaqiao University, Xiamen 361021, China;2. Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou 350108, China |
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| Abstract: | An efficient protocol for the synthesis of asymmetric 1,3-diketones was reported through diacylation of 1,1-diborylalkanes using two different acyl sources. In this transformation, an enolate boron species was initially formed by introducing an acyl group, then it was trapped by another acyl group to form 1,3-diketone. This method not only provided the gateway to obtain a series of 1,3-diketones, but also afforded an operationally simple and efficient access to pyrazoles and isoxazoles. |
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| Keywords: | 1 1-Diborylalkanes Diacylation Enolate boron species Boron-stabilized carbanion intermediates 1 3-Diketones |
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