Copper(II) complexes containing chiral substituted 2-(4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-one-2-yl)pyridine ligands: Synthesis, X-ray structural studies and asymmetric catalysis |
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Institution: | a Department of Organic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nám. ?s. legií 565, 532 10 Pardubice, Czech Republic b Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague 2, Czech Republic c Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Nám. ?s. legií 565, 532 10 Pardubice, Czech Republic |
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Abstract: | New chiral N,N-bidentate ligands derived from substituted 2-(4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-one-2-yl)pyridines have been prepared and characterised by means of 1H, 13C NMR spectroscopy and optical rotation. Their Cu(II) complexes were characterized by means of elemental analysis, 1H NMR spectroscopy and MS. By means of X-ray diffraction, molecular geometry of the complex of 2-(1-methyl-4-isopropyl-4-methyl-4,5-dihydro-1H-imidazol-5-one-2-yl)pyridine with copper(II) chloride was determined. The complex exhibits heterochiral dimeric arrangement of two square pyramids with one terminal and one bridge-forming chlorine atoms and two nitrogen atoms in the bases of the pyramids. The tops of these pyramids are formed by the remaining chlorine atoms. The complexes prepared catalyse the Henry reaction with the overall yields of 41-97% and with the maximum enantioselective excess of 19%. |
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Keywords: | 4 5-Dihydro-1H-imidazol-5-one ligands Copper complexes Asymmetric catalysis Henry reaction |
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