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http://dx.doi.org/10.14478/ace.2014.1089

Synthesis of Optically Active Monoesters via Kinetic Resolution by Chiral Co (Salen) Complex Immobilized on Mesoporous BEA  

Choi, Seong Dae (Department of Chemical Engineering, Inha University)
Park, Geun Woo (Department of Chemical Engineering, Inha University)
Lee, Gyung Chan (Department of Chemical Engineering, Inha University)
Kim, Geon-Joong (Department of Chemical Engineering, Inha University)
Publication Information
Applied Chemistry for Engineering / v.26, no.2, 2015 , pp. 132-137 More about this Journal
Abstract
BEA-zeolite was modified by alkaline solution to introduce mesoporosity in the crystals and the homogeneous chiral Co(III) salen was immobilized in the mesopores. The dinuclear chiral Co(salen)-$GaCl_3$ catalyst immobilized on mesoporous BEA-zeolite showed high activity for the regioselective ring opening of terminal epoxides by carboxylic acids. Various chiral monoester derivatives could be synthesized with moderate enantioselectivity (47~69 ee%) from racemic epoxides through above reaction. When the chiral (S)-ECH was used as a reactant, it was efficiently resolved by carboxylic acid with a high enantioselectivity in the presence of heterogenized chiral salen catalyst, and the ring opened product afforded optically pure monoester epoxide (R)-GB (up to 98 ee%) through the ring closing in the basic solution by elimination of HCl. The heterogeneous catalyst could be fabricated easily, and the catalytic activity was retained for several times reuse without any further regeneration step.
Keywords
chiral salen; immobilization; mesoporous BEA-zeolite; glycidyl butylate; nucleophile;
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