Development of Macroporous Polymer Monolith Immobilizing L-Proline-Based Organocatalyst and Application to Flow Asymmetric Aldol Addition Reaction

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  • Hattori Haruka
    Faculty of Engineering Department of Chemical Engineering, Kyushu University
  • Matsumoto Hikaru
    Faculty of Engineering Department of Chemical Engineering, Kyushu University
  • Hoshino Yu
    Faculty of Engineering Department of Chemical Engineering, Kyushu University
  • Miura Yoshiko
    Faculty of Engineering Department of Chemical Engineering, Kyushu University

Bibliographic Information

Other Title
  • 有機分子触媒L-prolineを固定化した多孔質高分子モノリスの開発およびフロー不斉アルドール付加反応への応用
  • ユウキ ブンシ ショクバイ L-proline オ コテイカ シタ タコウシツ コウブンシ モノリス ノ カイハツ オヨビ フロー フセイ アルドール フカ ハンノウ エ ノ オウヨウ

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<p>Flow process has attracted attention in the field of fine chemical synthesis. The well-designed immobilized catalyst is powerful tool to realize practical and efficient flow process. A macroporous monolith is a self-standing material with three-dimensional through-pores which ensures large surface area and high permeability. In this study, polyacrylamide-based macroporous monolith containing L-proline was developed and the porous properties of the monolith was evaluated. The internal structure of monolith was controlled by alcohol (ethanol, 1-butanol, 1-octanol, 1-dodecanol) used as porogen. In addition, the monolith was applied to asymmetric aldol addition reaction in flow system and achieved enantioselectivity of 61–74% ee at residence time of 12 h. This is the first example that achieved flow asymmetric synthesis using porous polymer monolith with L-proline.</p>

Journal

  • KAGAKU KOGAKU RONBUNSHU

    KAGAKU KOGAKU RONBUNSHU 46 (3), 77-83, 2020-05-20

    The Society of Chemical Engineers, Japan

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