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Enantioselective addition of diethylzinc to aldehydes using immobilized chiral BINOL–Ti complex on ordered mesoporous silicas
Institution:1. Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11 000 Belgrade, Serbia;2. Institute for Chemistry, Technology and Metallurgy, University of Belgrade, Studentski trg 14-16, 11 000 Belgrade, Serbia;3. Faculty of Chemistry, University of Belgrade, Studentski trg 14-16, 11 000 Belgrade, Serbia;1. Departamento de Química-Física, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de la Merced s/n, 37008-Salamanca, España;2. Laboratory of Catalysis and Materials - Associate Laboratory LSRE/LCM, Faculty of Engineering, University of Porto, rua Dr. Roberto Frias, 4200-465 Porto, Portugal;1. Instituto de Química Física – Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, San Lorenzo 456, 4000 Tucumán, Argentina;2. INQUINOA UNT CONICET, Ayacucho 471, 4000 Tucumán, Argentina;3. Institut für Physikalische und Theoretische Chemie, Universität Tübingen, 72076 Tübingen, Germany
Abstract:A chiral (S)-BINOL ligand has been covalently grafted on ordered mesoporous silicas—MCM-41 and SBA-15 and the resulting inorganic–organic hybrid materials used as chiral auxiliaries in Ti-promoted enantioselective addition of diethyl zinc to aldehydes under heterogeneous conditions. These heterogeneous catalysts showed promising activity and enantioselectivity. The catalyst having a larger pore diameter with capping of free silanol moiety with trimethylsilyl (TMS) group was found to be more active with enantioselectivities up to 81% being achieved. The catalyst worked well up to three cycles with retention of enantioselectivity after washing with 10% HCl in methanol.
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