Chiral amino-urea derivatives of (1R,2R)-1,2-diaminocyclohexane as ligands in the ruthenium catalysed asymmetric reduction of aromatic ketones by hydride transfer |
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| Institution: | 1. School of Pharmaceutical Engineering, China Pharmaceutical University, No. 639 Longmian Avenue, Nanjing 211816, China;2. School of Pharmaceutical Science, Nanjing Technology University, No. 30 Puzhu South Road, Nanjing 211816, China;3. College of Biotechnology and Pharmaceutical Engineering, Nanjing Technology University, No. 30 Puzhu South Road, Nanjing 211816, China;1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmans’ka str., Kyiv 02660, Ukraine;2. Department of Organic Chemistry, National Technical University of Ukraine “Kyiv Polytechnic Institute”, 37, Prospect Peremogy, Kyiv 03056, Ukraine;1. Department of Applied Chemistry, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan;2. Department of Organic Chemistry I, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain;3. IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain;4. Aix Marseille Université, Ecole Centrale Marseille, CNRS, ISM2 UMR7313, 13397 Cedex 20 Marseille, France;1. Center for Integrated Molecular Brain Imaging (CIMBI), Rigshospitalet and University of Copenhagen, Blegdamsvej 9, 2100 Copenhagen, Denmark;2. Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark;1. Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovak Republic;2. Materials Research Centre, Faculty of Chemistry, Brno University of Technology, Purkyňova 464, 612 00 Brno, Czech Republic;3. Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovak Republic;4. Institute of Physics, Slovak Academy of Sciences, Dúbravská cesta 9, 845 11 Bratislava, Slovak Republic;5. Institute of Electronics and Photonics, Slovak University of Technology, Ilkovičova 3, 812 19 Bratislava, Slovak Republic;6. Department of Physical Chemistry, Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic;7. Institute of Nuclear and Physical Engineering, Slovak University of Technology, Ilkovičova 3, 812 19 Bratislava, Slovak Republic |
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| Abstract: | Several new chiral urea and thiourea ligands have been prepared by reaction of (1R,2R)-1,2-diaminocyclohexane with various organic isocyanates and isothiocyanates. These were used as ligands in the ruthenium catalysed enantioselective reduction of aromatic ketones by isopropanol. The reduction proceeded at room temperature using 2 mol% of ruthenium catalyst to give good yields of the (R)-alcohol with enantiomeric excesses of up to 83%. By contrast, the use of bis-urea ligands gave much lower enantioselectivities. Amino-thiourea ligands led to the (S)-alcohol with low enantiomeric excess. |
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