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A new type of L-Tertiary leucine-derived ligand: Synthesis and application in Cu(II)-catalyzed asymmetric Henry reactions
Institution:1. Department of Chemistry, School of Pharmacy, The Fourth Military Medical University, Xi''an, 710032, People''s Republic of China;2. Key Laboratory of Functional Polymer Materials (Ministry of Education), Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People''s Republic of China;1. College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China;2. Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, Chengdu 610052, China;3. Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China;1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic;2. Institute of Environmental and Chemical Engineering, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic;1. School of Light Industry and Chemical Engineering, Dalian Polytechnic University, Dalian, 116034, China;2. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China;1. School of Chemical Engineering, University of Science and Technology Liaoning, 185 Qianshan Zhong Road, Anshan, Liaoning 114051, PR China;2. School of Material and Metallurgy, University of Science and Technology Liaoning, 185 Qianshan Zhong Road, Anshan, Liaoning 114051, PR China;3. Key Laboratory for Functional Material, Educational Department of Liaoning Province, University of Science and Technology Liaoning, Anshan, Liaoning 114051, PR China
Abstract:A new series of Schiff bases derived from amino acids were developed as chiral ligands for Cu(II)-catalyzed asymmetric Henry reactions. The optimum ligand 7d exhibited outstanding catalytic efficiency in the Cu(II)-catalyzed asymmetric Henry additions of four nitroalkanes to different kinds of aldehydes to produce 76 desired adducts in high yields (up to 96%) with excellent enantioselectivities, up to 99% enantiomeric excess (ee).
Keywords:Chirality  Copper complexes  Henry reaction  Schiff base ligands
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