The synthesis of dendritic BINOL ligands and their applications in the enantioselective Lewis acid catalyzed addition of diethylzinc to aldehydes |
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| Institution: | 1. LMRSS, Center for Molecular Science, Institute of Chemistry, The Chinese Academy of Sciences, Beijing 100080, China;2. Open Laboratory of Chirotechnology and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hong Kong, China;1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China;2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300171, PR China;1. Taksasago International Corporation, 4-11, Nishi-Yawata 1-Chome, Hiratsuka City, Kanagawa 254-0073, Japan;2. Department of Food and Cosmetic Science, Faculty of Bioindustry, Tokyo University of Agriculture, 196, Yasaka, Abashiri City, Hokkaido 099-2493, Japan;3. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan;1. Centro de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal;2. CQE, Instituto Superior Técnico, Universidade de Lisboa, Av, Rovisco Pais, 1049-001 Lisboa, Portugal;1. School of Chemistry and Chemical Engineering, Anhui University of Technology, Maanshan 243002, PR China;2. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, Fujian, PR China |
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| Abstract: | Novel dendritic chiral BINOL ligands have been synthesized through coupling of MOM-protected 3,3′-dihydroxymethyl-binaphthol with Fréchet-type polyether benzyl bromide dendrons followed by deprotection of the MOM groups using TsOH. These dendritic chiral BINOL ligands were found to be effective in the enantioselective addition of diethylzinc to benzaldehyde both in the presence and absence of Ti(O-iso-Pr)4. The enantioselectivity decreased with increasing generation in both cases. In the latter case, the dendritic chiral BINOL ligands showed much higher catalytic activity and enantioselectivity than BINOL. |
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