New chiral phosphorus catalysts derived from (S)-binaphthol for highly enantioselective reduction of acetophenone by borane |
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| Institution: | 1. Institute of Elemento-Organic Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China;2. Department of Applied Biology and Chemical Technology, the Hong Kong Polytechnic University, Hong Kong;1. State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS), Shanghai 200032, China;2. Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China;3. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, SIOC, CAS, Shanghai 200032, China;1. Reset Therapeutics, 260 Littlefield Avenue, Suite 200, South San Francisco, CA 94080, USA;2. Synterys Inc., 29540 Kohoutek Way, Union City, CA 94587, USA;1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran;2. Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran;1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, PR China;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS. 345 Lingling Road, Shanghai, 200032, PR China;1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA;2. Kavli Energy Nanoscience Institute, University of California, Berkeley, Berkeley, CA 94720, USA;3. Berkeley Global Science Institute, Berkeley, CA 94720, USA;4. BCMaterials, Basque Center for Materials, UPV/EHU Science Park, Leioa 48940, Spain;5. Ikerbasque, Basque Foundation for Science, Bilbao 48013, Spain |
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| Abstract: | New chiral (+)-2,2′-O,O-(1,1′-binaphthyl)-dioxo-N,N-diethylphospholidine 1 and its borane complex 3 were prepared from (S)-binaphthol and their use as catalysts in enantioselective borane reductions of prochiral acetophenone were investigated. Enantiomeric excesses of up to 98.5% have been obtained using 6 mol% of 1 at room temperature and using 6 mol% of 3 at 100°C. |
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