Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2617-2639.DOI: 10.6023/cjoc202401011 Previous Articles Next Articles
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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,*()
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:
Luyi Chena, Mengxia Tana, Jia'nan Jina, Zibin Zhanga, Feihe Huangb,c, Shijun Lia(), Yunxia Lia()
Received:
2024-01-12
Revised:
2024-03-18
Published:
2024-04-10
Contact:
Shijun Li, Yunxia Li
Supported by:
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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.
Entry | Guest | 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) |
Entry | Guest | 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) |
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 | [ |
CC5 | Chiral alcohols, esters, ethers and epoxides | [ |
CC6 | Chiral alcohols, esters, ketones, ethers, halohydrocarbons, epoxides, and organic acids | [ |
CC8 | Chiral alcohols, esters, ethers, and epoxides | [ |
CC11-R | Derivatized amino acids, alcohols, alcohol amines, esters, ethers, ketones, and epoxides | [ |
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 | [ |
CC5 | Chiral alcohols, esters, ethers and epoxides | [ |
CC6 | Chiral alcohols, esters, ketones, ethers, halohydrocarbons, epoxides, and organic acids | [ |
CC8 | Chiral alcohols, esters, ethers, and epoxides | [ |
CC11-R | Derivatized amino acids, alcohols, alcohol amines, esters, ethers, ketones, and epoxides | [ |
Analyte | Resolution | Separation factor | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
CC3-Ra | CC3-Sb | CC51-Rc | 225d | Be | CC3-Ra | CC3-Sb | CC51-Rc | 225d | Be | ||
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 |
Analyte | Resolution | Separation factor | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
CC3-Ra | CC3-Sb | CC51-Rc | 225d | Be | CC3-Ra | CC3-Sb | CC51-Rc | 225d | Be | ||
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 |
Entry | Catalyst | Time/d | Yield/% | anti/syn | ee/% |
---|---|---|---|---|---|
1 | CC31a | 1 | 98 | 88∶12 | 83 |
2 | CC32a | 2 | 99 | 93∶7 | 92 |
3 | BPP | 4 | 96 | 89∶11 | 88 |
4 | L-Proline | 10 | 80 | 45∶45 | 77 |
5 | CC31b | 1 | 97 | 88∶12 | -83 |
6 | CC32b | 2 | 98 | 93∶7 | -91 |
Entry | Catalyst | Time/d | Yield/% | anti/syn | ee/% |
---|---|---|---|---|---|
1 | CC31a | 1 | 98 | 88∶12 | 83 |
2 | CC32a | 2 | 99 | 93∶7 | 92 |
3 | BPP | 4 | 96 | 89∶11 | 88 |
4 | L-Proline | 10 | 80 | 45∶45 | 77 |
5 | CC31b | 1 | 97 | 88∶12 | -83 |
6 | CC32b | 2 | 98 | 93∶7 | -91 |
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