Synthesis of cis-1,2-diol-type chiral ligands and their dioxaborinane derivatives: Application for the asymmetric transfer hydrogenation of various ketones and biological evaluation |
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Authors: | Ahmet Kilic Tuğba Ersayan Balci Nevin Arslan Murat Aydemir Feyyaz Durap Veysi Okumuş Recep Tekin |
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Affiliation: | 1. Art and Science Faculty, Chemistry Department, Harran University, Sanliurfa, 63190 Turkey;2. Department of Field Crops, Faculty of Agriculture, Şırnak University, Şırnak, 73000 Turkey;3. Department of Chemistry, Science Faculty, Dicle University, Diyarbakir, 21280 Turkey;4. Department of Biology, Faculty of Science and Art, University of Siirt, Siirt, 56100 Turkey;5. Department of Infectious Diseases and Clinical Microbiology, DicleUniversity Faculty of Medicine, Diyarbakir, 21280 Turkey |
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Abstract: | Two cis-1,2-diol-type chiral ligands (T 1 and T 2 ) and their tri-coordinated chiral dioxaborinane (T (1–2) B (1–2) ) and four-coordinated chiral dioxaborinane adducts with 4-tert-butyl pyridine sustained by N → B dative bonds (T (1–2) B (1–2) -N) were synthesized and characterized by various spectroscopic techniques such as NMR (1H, 13C, and 11B), FT-IR and UV–Vis spectroscopy, LC–MS/MS, and elemental analysis. It was suggested that both ferrocene and trifluoromethyl groups played key roles in the catalytic and biological studies because they could tune the solubility of the chiral dioxaborinane complexes and adjust the strength of intermolecular interactions. To assess the biological activities of newly synthesized chiral dioxaborinane compounds, DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, reducing power, antibacterial, DNA binding, and DNA cleavage activities were tested. Then, all chiral dioxaborinane complexes were investigated as catalysts for the asymmetric transfer hydrogenation of various ketones under suitable conditions. The results indicated that the chiral dioxaborinane catalysts performed well with high yields. |
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Keywords: | asymmetric transfer hydrogenation biological activitieschiral dioxaborinanesCis-1,2-diol-type chiral ligands |
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