Synthesis and Application of Chiral Organic Imine Molecular Cages

doi:10.6023/cjoc202401011

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2617-2639.DOI: 10.6023/cjoc202401011 Previous Articles Next Articles

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手性亚胺有机分子笼的合成及应用研究

陈璐怡^a, 谭梦霞^a, 金迦南^a, 张子彬^a, 黄飞鹤^b^,^c, 李世军^a^,^*(), 李云霞^a^,^*()

a 杭州师范大学材料与化学化工学院有机硅化学及材料技术教育部重点实验室杭州 311121
b 浙江大学化学系司徒塔特分子科学研究院杭州 310058
c 浙江大学杭州国际科创中心浙江-以色列自组装功能材料联合实验室杭州 311215

收稿日期:2024-01-12 修回日期:2024-03-18 发布日期:2024-04-10
通讯作者: 李世军, 李云霞
基金资助:
国家自然科学基金(21773052); 国家自然科学基金(22071040); 浙江省自然科学基金(LZ24B020005)

Synthesis and Application of Chiral Organic Imine Molecular Cages

Luyi Chen^a, Mengxia Tan^a, Jia'nan Jin^a, Zibin Zhang^a, Feihe Huang^b^,^c, Shijun Li^a(), Yunxia Li^a()

a College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121
b Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310058
c Zhejiang-Israel Joint Laboratory of Self-Assembling Functional Materials, ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311215

Received:2024-01-12 Revised:2024-03-18 Published:2024-04-10
Contact: Shijun Li, Yunxia Li
Supported by:
National Natural Science Foundation of China(21773052); National Natural Science Foundation of China(22071040); Natural Science Foundation of Zhejiang Province(LZ24B020005)

As a kind of novel porous materials, porous organic molecular cages (POCs) exhibit excellent properties in the field of molecular recognition, gas storage and separation, catalysis and sensing. Moreover, their good solubilities make them easily fabricate composite materials to obtain more complicated structures and interesting performances. As one of main family members of POCs, organic imine molecular cages based on dynamic imine bonds have been extensively studied. Among them, chiral organic imine molecular cages have exhibited the wide applications of POCs in the fields such as chiral recognition, enantiomer separation, asymmetric catalysis, and so on. In order to provide a comprehensive overview of the synthesis and applications of chiral organic imine molecular cages, three effective synthetic strategies of chiral organic imine molecular cages, including direct synthesis by using enantiopure chiral building blocks, chiral assembly with achiral building blocks under the effect of symmetry breaking, and chiral self-sorting assembly with racemic building blocks, are summarized. The recent progresses of the applications of chiral organic molecular imine cages in the fields of chiral molecular recognition, chiral chromatographic separation and asymmetric catalysis are also briefly retrospected.

Key words: porous organic molecular cage, chirality, imine, synthetic strategy, self-assembly

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Luyi Chen, Mengxia Tan, Jia'nan Jin, Zibin Zhang, Feihe Huang, Shijun Li, Yunxia Li. Synthesis and Application of Chiral Organic Imine Molecular Cages[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2617-2639.

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Fig. & Tab. 32

Scheme 1. Synthesis of imine cages CC1, CC2, CC3-R and CC4-S

Scheme 2. Synthesis of chiral imine cages CC5~CC10

Scheme 3. Synthesis of chiral imine cages CC11-R, CC12-R, CC13-R and CC14-S

Scheme 4. Synthesis of chiral imine cage CC15 and CC16

Scheme 5. Synthesis of chiral phosphate imine cage CC17

Figure 1. (a) Chemical structure of linear tetraaldehyde precursors 18~20 and (b) side view and view through the cage windows of CC18~CC20 obtained from single-crystal X-ray structures (R cage enantiomers are shown) (Hydrogen atoms and solvent molecules are removed for clarity)

Scheme 6. Synthesis of chiral imine cages CC21 and CC22

Scheme 7. (a) Solution-phase synthesis of chiral imine cages CC23~CC26, and (b) chemical structures of the four cages CC23-S, CC24-R, CC25-R and CC26-R

Scheme 8. Synthesis of homochiral imine cages (S)-CC273＋ and (R)-CC273＋

Scheme 9. Synthesis of homochiral imine cages CC28-R and CC28-S

Scheme 10. Synthesis of homochiral imine cages CC29 and CC30

Scheme 11. Synthesis and structure of chiral imine cages CC31 and CC32 (Hydrogen atoms are omitted for clarity)

Scheme 12. Synthesis of helically chiral imine cages M,M,M-CC33 and P,P,P-CC33

Scheme 13. Synthesis of axially chiral imine cages (R)/(S)-CC34, and the amine cages (R)/(S)-CC34R

Scheme 14. Synthesis of heterochiral imine cages (S,R)-CC35 and (R,S)-CC35

Scheme 15. Synthesis of chiral face-rotating imine cages CC36 and CC37

Figure 2. 3D chiral polyhedral cages originated from 2D chiral facial units

Figure 3. (a) Synthesis of chiral face-rotating imine cages CC38 and CC39, and (b) cartoons to show the TPE con?gurations in the homodirectional cubes (6P)-CC38 and (6M)-CC38, and the heterodirectional cubes (4P2M)-CC39 and (2P4M)-CC39

Scheme 16. Synthesis of chiral face-rotating imine cages CC40 and CC41

Scheme 17. Synthesis of chiral imine cages CC42~CC44

Scheme 18. Synthesis of homochiral imine cages CC45 and heterochiral imine cage CC46

Scheme 19. Synthesis of homochiral imine cages (P)-CC47, (M)-CC47 and heterochiral imine cage (P,M)-CC48

Scheme 20. Synthesis of homochiral imine cages CC49 (butyl groups are omitted for clarity)

Scheme 21. Synthesis of homochiral radical imine cages CC50 and its precursor 49

Entry	Host	ee/%
1	M,M,M-CC33	60 (S)
2	P,P,P-CC33	58 (R)
3	M,M,M-CC33	84 (S)
4	P,P,P-CC33	67 (R)
5	M,M,M-CC33	23 (S)
6	P,P,P-CC33	20 (R)
7	34	1 (S)
8	34	2 (R)

Table 1. Data of chiral adsorption experiments

CSP	Types of chiral substances separated	Ref.
CC3-R	Chiral alcohols, diols, amines, alcohol amines, esters, ketones, ethers, halohydrocarbons, organic acids, amino acid methyl esters, sulfoxides and linear alkanes	[55, 56]
CC5	Chiral alcohols, esters, ethers and epoxides	[57]
CC6	Chiral alcohols, esters, ketones, ethers, halohydrocarbons, epoxides, and organic acids	[58]
CC8	Chiral alcohols, esters, ethers, and epoxides	[59]
CC11-R	Derivatized amino acids, alcohols, alcohol amines, esters, ethers, ketones, and epoxides	[60]

Table 2. Types of chiral substances on the chiral imine cage-coated GC capillary column

Scheme 22. Green synthesis of homochiral imine cages CC3-R, CC3-S and CC51-R

Analyte	Resolution					Separation factor
Analyte	CC3-R^a	CC3-S^b	CC51-R^c	225^d	B^e	CC3-R^a	CC3-S^b	CC51-R^c	225^d	B^e
Butan-2-ol	1.53	1.52	1.73	1.55	—	1.9	1.9	1.6	1.1	1.0
3-Butyn-2-ol	1.49	1.46	2.67	2.14	0.42	1.5	1.4	1.6	1.1	1.1
4-Heptyn-2-ol	—	—	1.82	—	—	1.0	1.0	1.4	1.0	1.0
Nonan-3-ol	—	—	1.51	—	—	1.0	1.2	1.4	1.0	1.0
5-Hexyn-3-ol	0.81	0.76	1.47	—	—	1.4	1.4	1.2	1.0	1.0
4-Penten-2-ol	0.65	0.57	1.56	—	—	1.3	1.2	1.3	1.0	1.0

Table 3. Resolution and separation factor for the separation of selected chiral alcohols on CC3-R, CC3-S, CC51-R, Cyclosil-B and β-DEX 225

Figure 4. CSPs CSP-1 and CSP-2 based on CC23-R

Entry	Catalyst	Time/d	Yield/%	anti/syn	ee/%
1	CC31^a	1	98	88∶12	83
2	CC32^a	2	99	93∶7	92
3	BPP	4	96	89∶11	88
4	L-Proline	10	80	45∶45	77
5	CC31^b	1	97	88∶12	－83
6	CC32^b	2	98	93∶7	－91

Table 4. Asymmetric aldol reactions catalyzed by chiral imine cages and related catalysts

Scheme 23. Synthesis of chiral imine cages CC52, CC53 and amine cages CC52R, CC53R

Scheme 24. Asymmetric Michael additions catalyzed by CC52R-Ni and CC53R-Ni

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手性亚胺有机分子笼的合成及应用研究

Synthesis and Application of Chiral Organic Imine Molecular Cages

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