Novel nitrogen ligands based on imidazole derivatives and their application in asymmetric catalysis |
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| Institution: | 1. Department of Organic Chemistry, University of Pardubice, nám. ?s. Legií 565, Pardubice 53210, Czech Republic;2. Department of Analytical Chemistry, University of Pardubice, nám. ?s. Legií 565, Pardubice 53210, Czech Republic;1. Henan Key Laboratory of Polyoxometalate, Institute of Molecule and Crystal Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, PR China;2. Nanyang Tobacco Monopoly Bureau (Company), Nanyang 473000, PR China;1. School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran;2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran;3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran;4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran;5. Department of Pharmacology, Faculty of Medical Sciences, Babol University of Medical Sciences, Babol, Iran;6. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran;1. School of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, P. R. China;2. State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. China |
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| Abstract: | Recently prepared chiral amines have been used in the preparation of novel tridentate ligands based on an imidazole ring with an additional (hetero)ring. The synthesis was carried out by the reaction of chiral amines with suitable aldehydes (2-phenylimidazole-4-carbaldehyde, 2-hydroxybenzaldehyde or pyridine-2-carbaldehyde) under reductive conditions (H2/Pd or NaBH4). All ligands prepared showed strong hydrogen bonds in d6-DMSO solution, which resulted in hindered imidazole tautomerism. The observed hindered tautomerism was studied by 1H NMR spectroscopy. The structures of the prepared ligands were also confirmed by APCI mass spectroscopy. Both chiral amines and tridentate compounds have been applied as ligands in copper (II)-catalyzed nitroaldol reactions (Henry reaction). Various reaction conditions for the Henry reaction have been studied (influence of temperature, molar ratio, solvent or copper (II) precursors). The compounds prepared with the two imidazole rings showed fast reaction times and a reversal in enantioselectivity compared to other chiral amines. |
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