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Constructing chiral diazoacetoacetates by enantioselective catalytic Mukaiyama aldol reactions
Affiliation:1. Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong;2. Department of Chemistry, Faculty of Science, Kyoto University, Japan;1. PGRD La Jolla, Medicinal Chemistry Department, 10770 Science Center Drive, San Diego, CA 92121, United States;2. Wuxi AppTec, Shanghai 200131, China;1. Polymer Synthesis and Analysis Laboratory, Department of Chemistry, Çanakkale Onsekiz Mart University, 17020 Çanakkale, Turkey;2. Secondary Science and Mathematics Education, Faculty of Education, Çanakkale Onsekiz Mart University, 17100 Çanakkale, Turkey;1. Key Laboratory of Luminescence and Optical Information, Ministry of Education, Beijing Jiaotong University, Beijing 100044, People׳s Republic of China;2. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian National Laboratory for Clean Energy, 457 Zhongshan Road, Dalian 116023, People׳s Republic of China;3. Key Laboratory of Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science and Technology, Nanjing 210094, People׳s Republic of China
Abstract:Asymmetric catalysis of Mukaiyama aldol addition reactions of methyl 3-TMSO-2-diazo-3-butenoate 4 with aromatic aldehydes using AgF/(R)-BINAP at −20 °C produces chiral diazoacetoacetates in high chemical yields and with high enantiocontrol.
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