Synthesis and Applications of Cinchona Squaramide-Modified Poly(Glycidyl Methacrylate) Microspheres as Recyclable Polymer-Grafted Enantioselective Organocatalysts.,Chemistry - A European Journal

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Synthesis and Applications of Cinchona Squaramide-Modified Poly(Glycidyl Methacrylate) Microspheres as Recyclable Polymer-Grafted Enantioselective Organocatalysts.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-07-22 , DOI: 10.1002/chem.202001993
Sándor Nagy ₁ , Zsuzsanna Fehér ₁ , Levente Kárpáti _{2,

3} , Péter Bagi ₁ , Péter Kisszékelyi ₁ , Béla Koczka ₄ , Péter Huszthy ₁ , Béla Pukánszky ₂ , József Kupai ₁

Affiliation

This work presents the immobilization of cinchona squaramide organocatalysts on poly(glycidyl methacrylate) solid supports. Preparation of the well‐defined monodisperse polymer microspheres was facilitated by comprehensive parameter optimization. By exploiting the reactive epoxy groups of the polymer support, three amino‐functionalized cinchona derivatives were immobilized on this carrier. To explore the effect of the amino linker, these structurally varied precatalysts were synthesized by modifying the cinchona skeleton at different positions. The catalytic activities of the immobilized organocatalysts were tested in the Michael addition of pentane‐2,4‐dione and trans‐β‐nitrostyrene with excellent yields (up to 98 %) and enantioselectivities (up to 96 % ee). Finally, the catalysts were easily recovered five times by centrifugation without loss of activity.

中文翻译：

金鸡纳方酰胺改性聚甲基丙烯酸缩水甘油酯微球作为可回收聚合物接枝对映选择性有机催化剂的合成及应用。

这项工作介绍了金鸡纳方酰胺有机催化剂在聚（甲基丙烯酸缩水甘油酯）固体载体上的固定化。通过全面的参数优化，促进了结构清晰的单分散聚合物微球的制备。通过利用聚合物载体的反应性环氧基团，将三种氨基官能化的金鸡纳衍生物固定在该载体上。为了探索氨基连接体的作用，通过在不同位置修饰金鸡纳骨架来合成这些结构不同的预催化剂。在戊烷-2,4-二酮和反式-β-硝基苯乙烯的迈克尔加成中测试了固定化有机催化剂的催化活性，具有优异的产率（高达 98%）和对映选择性（高达 96% ee）。最后，催化剂可以通过离心轻松回收五次而不会损失活性。

更新日期：2020-07-22

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