• Title/Summary/Keyword: Regioselective epoxide ring-opening

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Synthesis of Optically Active Monoesters via Kinetic Resolution by Chiral Co (Salen) Complex Immobilized on Mesoporous BEA (메조세공 BEA에 고정화된 키랄 Co살렌 착체의 동적분할을 통한 고광학순도의 키랄 모노에스테르 합성)

  • Choi, Seong Dae;Park, Geun Woo;Lee, Gyung Chan;Kim, Geon-Joong
    • Applied Chemistry for Engineering
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    • v.26 no.2
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    • pp.132-137
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    • 2015
  • 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.