手性大环化合物在超分子催化中的研究进展及应用

doi:10.6023/cjoc202502040

摘要/Abstract

催化技术在现代科学和工业中具有不可替代的重要意义, 并在生物医药、绿色化学等方面发挥了重要作用. 大环化合物因其独特的分子识别能力以及通过非共价相互作用形成包合复合物的特性, 展现出高效的催化剂性能. 其中, 手性大环化合物凭借其手性特征, 能够实现高效的手性诱导和选择性识别. 其内部空腔可容纳底物进行预组织排列, 从而促进高效的化学转化过程. 因此, 手性大环化合物作为超分子催化体系的理想平台, 在不对称催化中表现出优异的催化活性和选择性. 此文综述了近年来手性冠醚、手性环糊精、手性杯芳烃和手性柱芳烃等手性大环化合物在不对称催化中的研究进展和应用, 并期望为超分子不对称催化研究提供参考.

关键词: 主客体化学, 手性大环化合物, 超分子催化, 不对称合成

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

引用此文

黄胜兰, 杨留攀, 王力立, 姚欢. 手性大环化合物在超分子催化中的研究进展及应用[J]. 有机化学, 2025, 45(10): 3624-3643.

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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图/表 23

图1. 手性大环化合物作为催化剂的优势

Figure 1. Advantages of chiral macrocycles as catalysts

图2. 手性糖基冠醚催化苯乙酸甲酯与丙烯酸甲酯的Michael加成反应[55]

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

图3. N-糖基氮杂冠醚催化2-硝基丙烷对反式查尔酮的对映选择性加成反应[47,57]

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

图4. D-葡萄糖苷、D-甘露糖苷、D-半乳糖苷基手性冠醚催化的不对称合成反应[58,60,63]

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

图5. BINOL修饰的冠醚催化对映选择性Michael加成反应[47-67]

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

图6. 氮杂冠醚衍生的手性联醇催化烯基硼酸与α,β-不饱和酮的不对称Michael加成反应[71]

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]

图7. 3,3'-双(氮杂冠醚)-衍生的手性磷酸作为催化剂催化不对称缩醛化反应[72]

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

图8. 具有双氮冠醚骨架的手性二磷酰胺配体的不对称催化[75]

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

图9. 基于手性BINOL的寡聚乙二醇新型催化剂催化α-羰基醛不对称合成手性α-羟基硫酯[76]

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

图10. 环糊精衍生物催化不对称Aldol反应和MBH碳酸酯的不对称烯丙基胺化反应[81-82]

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

图11. β-环糊精-NHC-金(I)络合物催化烷氧基环化反应[86]

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

图12. β-环糊精-NHC-金(Ⅰ)催化1,5-烯炔环异构化反应[87]

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

图13. β-环糊精及其衍生物催化蒽甲酸的光二聚反应[104-106]

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

图14. 环糊精修饰的上转换纳米粒子用于光化学催化体系[109]

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

图15. γ-环糊精金属-有机框架用于催化AC的光二聚化反应[110]

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

图16. 固有手性杯[4]芳烃催化对映选择性[4＋2]环加成[129]

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

图17. 手性杯[4]芳烃衍生物成功实现了醛酮的Aldol反应[142]

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

图18. 基于樟脑磺酰基功能化冠醚-杯[4]芳烃用于催化不对称Strecker反应[143]

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

图 19. 平面手性柱[5]芳烃催化苯乙烯不对称硅氢化反应[159]

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

图20. 基于柱[5]芳烃的手性三维聚合网络催化二乙基锌和芳香醛的不对称加成反应[162]

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

图21. 四氨基-双硫脲手性大环催化环醛亚胺与β-酮酸的脱羧Mannich反应[20,85]

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

图22. 手性双硫脲大环化合物大环催化吲哚与亚胺的对映选择性Friedel-Crafts反应[22]

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

图23. 手性双磷酸大环催化色胺底物的对映选择性氟环化反应[180]

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

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