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Progress in Chemistry 2018, Vol. 30 Issue (5): 476-490 DOI: 10.7536/PC180137 Previous Articles   Next Articles

• Review •

Asymmetric Supramolecular Catalysis Based on Macrocyclic Host Molecules

Yuping Tang1,2, Yanmei He1*, Yu Feng1, Qinghua Fan1,2*   

  1. 1. CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences(CAS), Beijing 100190, China;
    2. School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, China
  • Received: Revised: Online: Published:
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21772204, 21373231, 21521002) and the Key Research Program of Frontier Sciences, CAS (No. QYZDJ-SSW-SLH023).
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In recent years, supramolecular catalysis has become one of the most challenging research frontiers and hot spots in organic synthesis based on the continuous combination and fusion of supramolecular chemistry and catalysis, and has achieved gratifying development. As the main objectives in supramolecular chemistry, macrocyclic host molecules have gained much attention in supramolecular catalysis due to their reversible recognition and self-assembly with different guest molecules and thus can realize pre-organization of reactants within the catalytic cavities. In the last 20 years, progress has been achieved in supramolecular catalysis based on macrocyclic host molecules. This review will focus on the recent progress in asymmetric supramolecular catalysis based on the representative macrocyclic host molecules, such as crown ethers, cyclodextrins, calixarenes, and their counterparts. The design and synthesis of chiral catalysts, the use of these catalysts in enantioselective reactions, especially, the supramolecular modulation of catalytic activity and selectivity via host-guest association will be introduced. Meanwhile, the limitation and drawbacks of current study and the perspectives for its future development will also be discussed.
Contents
1 Introduction
2 Asymmetric catalysis based on crown ethers and their counterparts
2.1 Chiral crown ether-based metal catalysts
2.2 Chiral metallacrown ether catalysts
2.3 Chiral pseudorotaxane and rotaxane catalysts
2.4 Podands in asymmetric catalysis
3 Asymmetric catalysis based on cyclodextrins
3.1 Cyclodextrin as macroreactor
3.2 Cyclodextrin-based metal catalysts
3.3 Cyclodextrin organocatalysts
4 Asymmetric catalysis based on chiral calixarenes
4.1 Chiral calixarene-based metal catalysts
4.2 Chiral calixarene-based organocatalysts
4.3 Inherently chiral calixarene catalysts
5 Conclusion and outlook
Key words: asymmetric catalysis, macrocyclic compound, host-guest recognition, supramolecular catalysis

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