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聚合物锚定金鸡纳生物碱:合成及其在有机催化中的应用

Polymer Anchored Cinchona Alkaloids: Synthesis and their Applications in Organo-Catalysis.

作者信息

Haripriya Patra, Rai Rajat, Vijayakrishna Kari

机构信息

Department of Chemistry, School of Basic Sciences, Indian Institute of Technology, Bhubaneswar, Odisha, 752050, India.

出版信息

Top Curr Chem (Cham). 2025 Apr 9;383(2):19. doi: 10.1007/s41061-025-00499-8.

Abstract

Cinchona alkaloids are naturally occurring chiral molecules that have emerged as catalysts in asymmetric organocatalysis especially in enantioselective transformations because of their inherent chirality and unique structural features. Immobilizing these alkaloids on polymeric supports has significantly influenced their use in catalysis. Polymer-anchored cinchona alkaloids combine the catalytic efficacy of cinchona derivatives with additional benefits of polymer chain, such as ease of recovery, recyclability, reusability, and reduced environmental impact. These polymer-supported cinchona alkaloids have found wide applications in enantioselective reactions such as Michael addition, aldol condensations, Henry reaction, dimerization reaction, dihydroxylation, and benzylation. Various strategies have been employed for anchoring cinchona alkaloids onto polymers, including covalent attachment of alkaloids in the polymer side chain or main chain, and ionic attachment of alkaloids via quaternization in the main chain or side chain of polymer. This review focuses on the various synthetic methodologies for the preparation of polymer-anchored cinchona alkaloids and their application in numerous asymmetric transformations.

摘要

金鸡纳生物碱是天然存在的手性分子,由于其固有的手性和独特的结构特征,已成为不对称有机催化中的催化剂,尤其是在对映选择性转化中。将这些生物碱固定在聚合物载体上显著影响了它们在催化中的应用。聚合物锚定的金鸡纳生物碱将金鸡纳衍生物的催化效能与聚合物链的额外优势相结合,如易于回收、可循环利用、可重复使用以及减少对环境的影响。这些聚合物负载的金鸡纳生物碱已在对映选择性反应中得到广泛应用,如迈克尔加成反应、羟醛缩合反应、亨利反应、二聚反应、二羟基化反应和苄基化反应。已采用多种策略将金鸡纳生物碱锚定到聚合物上,包括生物碱在聚合物侧链或主链中的共价连接,以及通过聚合物主链或侧链中的季铵化实现生物碱的离子连接。本综述重点关注制备聚合物锚定金鸡纳生物碱的各种合成方法及其在众多不对称转化中的应用。

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