Catalytic enantioselective synthesis of secondary alcohols using C2-symmetric diamino diol ligands |
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| Affiliation: | 1. Department of Chemistry, Panjab University, India;2. Department of Microbiology, Panjab University, Chandigarh 160014, India;3. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;1. Department of Chemistry, University of Kalyani, Kalyani, West Bengal 741235, India;2. Department of Chemical Sciences, Indian Institute of Science Education & Research Kolkata, Mohanpur, West Bengal 741246, India;3. Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India;4. Institut fur Anorganische Chemie und Analytische Chemie, Johannes-Gutenberg Universitat Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany;1. C4T (Colosseum Combinatorial Chemistry Centre for Technology) S.C.a r.l., Via della Ricerca Scientifica s.n.c., 00133 Rome, Italy;2. Department of Discovery, Dompé Farmaceutici SpA Research Center, via Campo di Pile, 67100 L’Aquila, Italy;3. Department of Discovery, Dompé Farmaceutici SpA, Research Center, via P. Castellino, 80131 Napoli, Italy;4. Department of Chemical Science and Technology, University of Rome ‘Tor Vergata’, 00133 Rome, Italy;1. MINOS-EMaS, Universitat Rovira i Virgili, Avda. Països Catalans 26, 43007 Tarragona, Spain;2. Central European Institute of Technology (CEITEC), Brno University of Technology, Technická 10, 616 00 Brno, Czech Republic;3. Scientific Service, Universitat Rovira i Virgil, Avda. Països Catalans 26, 43007 Tarragona, Spain;4. Division of Materials Chemistry, Faculty of Engineering, Hokkaido University, N-13, W-8, Sapporo 060-8628, Japan;1. Chemistry Department, University of Pretoria, Private Bag X20, Hatfield 0028, Pretoria, South Africa;2. Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg 2050, South Africa |
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| Abstract: | A new class of diamino diols was evaluated as catalytic ligands in the enantioselective borane reduction of aromatic ketones and the enantioselective ethylation of arylaldehydes with diethylzinc. By variation of the substitution pattern on the ketone, e.e.s of up to 94% could be obtained by in situ borane reduction using 0.025 equiv. of the ligand at 35°C in THF. N,N,N′,N′-Tetramethyldiamino diol and N,N′-dialkyl diamino diol were used as promoters for the enantioselective addition of diethylzinc reagent to the arylaldehyde, where use of 0.1 equiv. of N,N,N′,N′-tetramethyl diamino diol as catalyst in the addition of diethylzinc to arylaldehyde achieved e.e.s of up to 98%. |
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