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Asymmetric reduction of aromatic ketones in pyridinium-based ionic liquids
Affiliation:1. Department of Chemical Engineering, Kazakh-British Technical University, 050000 Almaty, Kazakhstan;2. Department of Chemistry, Faculty of Science, University of Dicle, 21280 Diyarbakir, Turkey;3. Department of Science, Faculty of Education, University of Dicle, 21280 Diyarbakir, Turkey;4. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Dicle University, Diyarbakir 21280, Turkey;5. Department of Chemistry, Faculty of Science and Art, University of İnönü, 44280 Malatya, Turkey;1. Department of Chemistry, Faculty of Arts and Sciences, American University of Beirut, Beirut, Lebanon;2. Department of Anatomy, Cell Biology and Physiology, Faculty of Medicine, American University of Beirut, Beirut, Lebanon;3. Medical Engineering Department, Faculty of Medicine, American University of Beirut Medical Center (AUBMC), Beirut, Lebanon;4. Department of Biology, Faculty of Sciences II, Lebanese University, Fanar, Lebanon;1. Department of Inorganic Chemistry, Wroclaw Medical University, Borowska 211A, 50-556 Wroclaw, Poland;2. Faculty of Chemistry, Wrocław Technical University of Technology, Wyspiańskiego 27, 50-373 Wrocław, Poland;3. Laboratory of Elemental Analysis and Structural Research, Wroclaw Medical University, Borowska 211A, 50-556 Wroclaw, Poland;1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary;2. Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary;3. Department of Biochemistry, University of Szeged, Dóm tér 9, H-6720 Szeged, Hungary
Abstract:
The asymmetric reduction of aromatic ketones has been studied in pyridinium-based room temperature ionic liquids, namely, 1-ethyl-pyridinium tetrafluoroborate, [EtPy]+[BF4] and 1-ethyl-pyridinium trifluoroacetate, [EtPy]+[CF3COO]. Ionic liquids were employed as solvents, while (R)-BINOL and (R)-BINOL-Br were used as chiral promoters. The effects of solvent, reaction time, temperature, catalyst loading and substituents were investigated. The reduction could be easily carried out in both ionic liquids with lower catalyst loading. 1-Ethyl-pyridinium tetrafluoroborate was recycled and reused efficiently.
Keywords:
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