Novel C2-symmetric chiral O,N,N,O-tetradentate 2,2-bipyridyldiolpropane ligands: synthesis and application in asymmetric diethylzinc addition to aldehydes |
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| Institution: | 1. Department of Chemistry, National Dong Hwa University, Soufeng, Hualien 974, Taiwan, ROC;2. Instrumentation Center, College of Science, National Taiwan University, Taipei 106, Taiwan, ROC;1. DIET University of Rome “La Sapienza”, via Eudossiana 18, 00184 Rome (Italy);2. SAE University of Rome “La Sapienza”, via Salaria 851/881, 00138 Rome (Italy);3. Department of Chemistry “G. Ciamician”, University of Bologna, via Selmi 2, 40126, Bologna (Italy);4. Department of Chemistry, University of Rome “La Sapienza”, piazzale A. Moro, 5, 00185 Rome (Italy);1. College of Chemistry and Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, Xiangtan University, Xiangtan 411105, PR China;2. Key Laboratory of Advanced Functional Polymeric Materials of College of Hunan Province, Xiangtan University, Xiangtan 411105, PR China;1. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia;2. Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands;1. Laboratory of Thermodynamics of Solutions of Non-electrolytes and Biologically Active Substances, G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 1 Akademicheskaya Str., 153045 Ivanovo, Russian Federation;2. Incorporated Physicochemical Center of Solution Researches, G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 1 Akademicheskaya Str., 153045 Ivanovo, Russian Federation;3. Department of Inorganic Chemistry, Ivanovo’s State University of Chemistry and Technology, 7 Sheremetevsky Ave., 153000 Ivanovo, Russian Federation;4. Laboratory of Nitrogen-containing Compounds, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 199119 Moscow, Russian Federation |
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| Abstract: | First synthesis of C2-symmetric chiral O,N,N,O-tetradentate 2,2-bipyridyldiolpropane ligands is described. The Mukaiyama–Michael reaction was applied as an important reaction for the synthesis of 2,2-bipyridylpropane 9. Among the ligands synthesized, ligand 11 exhibits excellent chiral induction (up to 97% ee) in diethylzinc addition to various aldehydes. The use of additional Lewis acid such as Ti(OiPr)4 in diethylzinc addition reaction is not required for the present catalytic system. |
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