Research Progress and Application of Chiral Macrocycles in Supramolecular Catalysis

doi:10.6023/cjoc202502040

Abstract

Catalytic technology holds irreplaceable significance in modern science and industry, and has played a crucial role in biomedicine, green chemistry, and other fields. Macrocycles, with their unique ability for molecular recognition and the formation of inclusion complexes through non-covalent interactions, exhibit highly efficient catalytic performance. Among them, chiral macrocycles, leveraging their chiral characteristics, can achieve efficient chiral induction and selective recognition. Their internal cavities can accommodate substrates for pre-organized arrangement, thereby facilitating efficient chemical transformations. Therefore, chiral macrocycles serve as an ideal platform for supramolecular catalytic systems, demonstrating excellent catalytic activity and selectivity in asymmetric catalysis. This review summarizes the research progress and applications of chiral macrocycles, such as chiral crown ethers, chiral cyclodextrins, chiral calixarenes, and chiral pillararenes, in asymmetric catalysis in recent years, and is expected to provide references for the study of supramolecular asymmetric catalysis.

Key words: host-guest chemistry, chiral macrocyclic compounds, supramolecular catalysis, asymmetric synthesis

Cite this article

Shenglan Huang, Liupan Yang, Lili Wang, Huan Yao. Research Progress and Application of Chiral Macrocycles in Supramolecular Catalysis[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3624-3643.

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Fig. & Tab. 23

Figure 1. Advantages of chiral macrocycles as catalysts

Figure 2. Michael addition reaction of methyl phenylacetate and methyl acrylate catalyzed by chiral glycosyl crown ether[55]

Figure 3. Enantioselective addition of 2-nitropropane to trans-chalcone catalyzed by N-glycosyl aza-crown ethers[47,57]

Figure 4. Asymmetric synthesis reactions catalyzed by D-glucose-, D-mannose- and D-galactose-based chiral crown ethers[58,60,63]

Figure 5. BINOL-modified crown ethers catalyzed enantioselective Michael addition reactions[47-67]

Figure 6. Catalytic asymmetric Michael addition of alkenyl boronic acids to α,β-unsaturated ketones by chiral bisphenol catalyst derived from aza-crown ether[71]

Figure 7. 3,3'-Bis(aza-crown ether)-derived chiral phosphoric acid as a catalyst for asymmetric acetalization[72]

Figure 8. Asymmetric catalysis with chiral diphosphoramidite ligands featuring a diaza-crown ether framework[75]

Figure 9. Chiral BINOL-based oligoethylene glycols catalysts for asymmetric synthesis of chiral α-hydroxythioesters from α-oxoaldehydes[76]

Figure 10. Cyclodextrin derivatives catalyzed the asymmetric Aldol reaction and the asymmetric allyl amination reaction of MBH carbonate[81-82]

Figure 11. β-Cyclodextrin-NHC-gold (I) complex catalyzed an alkoxy cyclization reaction[86]

Figure 12. β-Cyclodextrin-NHC-gold (I) catalyzed the isomerization of 1,5-enyne rings[87]

Figure 13. Photodimerization of anthracene carboxylic acid catalyzed by β-cyclodextrin and its derivatives[104-106]

Figure 14. UCNP-CDn for photochemical catalytic systems[109]

Figure 15. γ-Cyclodextrin metal-organic framework for catalytic photodimerization of AC[110]

Figure 16. Enantioselective [4＋2] cycloaddition catalyzed by intrinsically chiral calix[4]arene[129]

Figure 17. Chiral calix[4]arene derivatives successfully achie- ved Aldol reactions of aldehydes and ketones[142]

Figure 18. Catalyzing asymmetric strecker reaction with camphorsulfonate functionalized crown ether-calix[4]arene[143]

Figure 19. Asymmetric hydrosilylation of styrene catalyzed by planar chiral pillar[5]arene[159]

Figure 20. Chiral three-dimensional polymer networks based on pillar[5]arene catalyzed the asymmetric addition reaction of diethylzinc and aromatic aldehydes[162]

Figure 21. Tetraamino-bisthiourea chiral macrocycles catalyze the decarboxylative Mannich reaction of cyclic aldimine with β-ketoacids[20,85]

Figure 22. Chiral bis-thiourea macrocycles catalyze the enantioselective Friedel-Crafts reaction of indoles with imines[22]

Figure 23. Chiral diphosphate macrocycles catalyze the enantioselective fluorocyclization of tryptamine substrates[180]

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