Citation: Zhang Yongna, Duan Hui-Xin, Wang You-Qing. Research Progress in Asymmetric Reactions of Imines Using Chiral Primary Amines as Organocatalysts[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1514-1528. doi: 10.6023/cjoc201908030 shu

Research Progress in Asymmetric Reactions of Imines Using Chiral Primary Amines as Organocatalysts

College of Chemistry and Chemical Engineering, Henan Key Laboratory of Polyoxometalate Chemistry, Provincial Key Laboratory of Natural Medicine and Immuno-Engineering, Henan University, Kaifeng, Henan 475004

Corresponding author: Zhang Yongna, zhangyongna@henu.edu.cn Wang You-Qing, wyouqing@hotmail.com
Received Date: 22 August 2019
Revised Date: 1 November 2019
Available Online: 29 February 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. U1404211), and the Key Scientific and Technological Research Projects of Henan Education Department (No. 14A150029)the Key Scientific and Technological Research Projects of Henan Education Department 14A150029the National Natural Science Foundation of China U1404211

Figures(33)

Chiral primary amine is a kind of important small organic molecule catalyst in the field of asymmetric organocatalysis. Like secondary amine catalyst, primary amine can react with carbonyl compounds to form reactive intermediate of enamine or iminium to catalyze various asymmetric reactions, achieving excellent enantioselectivities. The catalytic asymmetric 1, 2-addition to the electrophilic C=N double bond of imines (involving imine intermediates in the reaction process) is the most efficient way to obtain nitrogen-containing compounds bearing α-chiral center. In recent years, the highly enantioselective asymmetric reaction of imines by chiral primary amine catalysts has made some progress, so this topic is summarized and prospected.
- chirality,
- primary amines,
- imines,
- asymmetric catalysis,
- organocatalysts
1. [1]
  Li, Y. M.; Fan, Q. H.; Chen, X. Z. Asymmetric Organic Reactions, Beijing Chemical Industry Press, Beijing, 2005 (in Chinese).
2. [2]
  Dalko, P. I. Comprehensive Enantioselective Organocatalysis:Catalysts, Reactions, and Applications, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2013.
3. [3]
  Jacobsen, E. N.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20618. doi: 10.1073/pnas.1016087107
4. [4]
  Maruoka, K.; List, B.; Yamamoto, H.; Gong, L.-Z. Chem. Commun. 2012, 48, 10703. doi: 10.1039/c2cc90327j
5. [5]
  Zhan, G.; Du, W; Chen, Y.-C. Chem. Soc. Rev. 2017, 46, 1675. doi: 10.1039/C6CS00247A
6. [6]
  Wurz, R. P. Chem. Rev. 2007, 107, 5570. doi: 10.1021/cr068370e
7. [7]
  Palomo, C.; Oiarbide, M.; López, R. Chem. Soc. Rev. 2009, 38, 632. doi: 10.1039/B708453F
8. [8]
  Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416. doi: 10.1021/cr068388p
9. [9]
  Notz, W.; Tanaka, F.; Barbas, C. F., Ⅲ Acc. Chem. Res. 2004, 37, 580. doi: 10.1021/ar0300468
10. [10]
  Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471. doi: 10.1021/cr0684016
11. [11]
  List, B.; Lerner, R. A.; Barbas, C. F., Ⅲ. J. Am. Chem. Soc. 2000, 122, 2395. doi: 10.1021/ja994280y
12. [12]
  Donslund, B. S.; Johansen, T. K.; Poulsen, P. H.; Halskov, K. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2015, 54, 13860. doi: 10.1002/anie.201503920
13. [13]
  Kano, T.; Maruoka, K. Chem. Sci. 2013, 4, 907 doi: 10.1039/C2SC21612D
14. [14]
  Xu, L.-W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807.
15. [15]
  Jiang, L.; Chen, Y.-C. Catal. Sci. Technol. 2011, 1, 354. doi: 10.1039/c0cy00096e
16. [16]
  Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 9748. doi: 10.1002/anie.201109036
17. [17]
  Zhang, L.; Luo, S. Synlett 2012, 1575. doi: 10.1055/s-0031-1290405
18. [18]
  Zhang, L.; Fu, N.; Luo, S. Acc. Chem. Res. 2015, 48, 986. doi: 10.1021/acs.accounts.5b00028
19. [19]
  Reddy, U. V. S.; Chennapuram, M.; Seki, C.; Kwon, E.; Okuyama, Y.; Nakano, H. Eur. J. Org. Chem. 2016, 4124.
20. [20]
  Luo, S.; Xu, H.; Li, J.; Zhang, L.; Cheng, J.-P. J. Am. Chem. Soc. 2007, 129, 3074. doi: 10.1021/ja069372j
21. [21]
  Xie, J.-W.; Chen, W.; Li, R.; Zeng, M.; Du, W.; Yue, L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2007, 46, 389. doi: 10.1002/anie.200603612
22. [22]
  Gefflaut, T.; Blonksi, C.; Perie, J.; Willson, M. Prog. Biophys. Molec. Biol. 1995, 63, 301. doi: 10.1016/0079-6107(95)00008-9
23. [23]
  Enders, D.; Reinhold, U. Tetrahedron:Asymmetry 1997, 1895. doi: 10.1002/chin.199745303
24. [24]
  Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626. doi: 10.1021/cr100204f
25. [25]
  Wang, D.; Hou, C.; Chen, L.; Liu, X.; An, Q.; Hu, X. Chin. J. Org. Chem. 2013, 33, 1355(in Chinese). doi: 10.6023/cjoc201211036
26. [26]
  Xie, J.-H.; Zhu, S.-F.; Zhou, Q.-L. Chem. Rev. 2011, 111, 1713. doi: 10.1021/cr100218m
27. [27]
  Qin, Y.; Lv, J.; Luo, S. Tetrahedron Lett. 2014, 55, 2423; doi: 10.1016/j.tetlet.2014.02.126
28. [28]
  Cheng, M.-X.; Yang, S.-D. Synlett 2017, 28, 159.
29. [29]
  Ibrahem, I.; Zou, W.; Engqvist, M.; Xu Y.; Córdova, A. Chem.-Eur. J. 2005, 11, 7024. doi: 10.1002/chem.200500746
30. [30]
  Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas Ⅲ, C. F. J. Am. Chem. Soc. 2007, 129, 288. doi: 10.1021/ja0677012
31. [31]
  Cheng, L.; Wu, X.; Lu, Y. Org. Biomol. Chem. 2007, 5, 1018. doi: 10.1039/b701579h
32. [32]
  Cheng, L.; Han, X.; Huang, H.; Wong, M. W.; Lu, Y. Chem. Commun. 2007, 4143.
33. [33]
  Dziedzic, P.; Córdova, A. Tetrahedron:Asymmetry 2007, 18, 1033. doi: 10.1016/j.tetasy.2007.04.024
34. [34]
  Zhang, H.; Ramasastry, S. S. V.; Tanaka, F.; Barbas Ⅲ, C. F. Adv. Synth. Catal. 2008, 350, 791. doi: 10.1002/adsc.200800069
35. [35]
  Westermann, B.; Neuhaus, C. Angew. Chem., Int. Ed. 2005, 44, 4077. doi: 10.1002/anie.200500297
36. [36]
  Zhang, G.; Ma, Y.; Wang, S.; Kong, W.; Wang, R. Chem. Sci. 2013, 4, 2645. doi: 10.1039/c3sc50604e
37. [37]
  Mondal, B.; Pan, S. C. Org. Biomol. Chem. 2014, 12, 9789. doi: 10.1039/C4OB02146K
38. [38]
  Zhang, S.; Li, L.; Hu, Y.; Zha, Z.; Wang, Z.; Loh, T.-P. Org. Lett, 2015, 17, 1050. doi: 10.1021/acs.orglett.5b00196
39. [39]
  Zhang, S.; Li, L.; Hu, Y.; Li, Y.; Yang, Y.; Zha, Z.; Wang, Z. Org. Lett. 2015, 17, 5036. doi: 10.1021/acs.orglett.5b02514
40. [40]
  Otsuki, T.; Kumagai, J.; Kohari, Y.; Okuyama, Y.; Kwon, E.; Seki, C.; Uwai, K.; Mawatari, Y.; Kobayashi, N.; Iwasa, T.; Tokiwa, M.; Takeshita, M.; Maeda, A.; Hashimoto, A.; Turuga, K.; Nakano, H. Eur. J. Org. Chem. 2015, 7292.
41. [41]
  Dai, J.; Xiong, D.; Yuan, T.; Liu, J.; Chen, T.; Shao, Z. Angew. Chem., Int. Ed. 2017, 56, 12697. doi: 10.1002/anie.201706304
42. [42]
  Chen, S.; Houk, K. N. J. Org. Chem. 2018, 83, 3171. doi: 10.1021/acs.joc.8b00037
43. [43]
  You, Y.; Zhang, L.; Cui, L.; Mi, X.; Luo, S. Angew. Chem., Int. Ed. 2017, 56, 13814. doi: 10.1002/anie.201707005
44. [44]
  You, Y.; Luo, S. Org. Lett. 2018, 20, 7137. doi: 10.1021/acs.orglett.8b03083
45. [45]
  Hou, H.; Zhu, S.; Atodiresei, I.; Rueping, M. Eur. J. Org. Chem. 2018, 1277.
46. [46]
  Yang, Q.; Zhang, J.; Jia, Z.; Yang, C.; Zhang, L.; Luo, S. Asian J. Org. Chem. 2019, 8, 1049. doi: 10.1002/ajoc.201900013
47. [47]
  Duan, J.; Li, P. Catal. Sci. Technol. 2014, 4, 311. doi: 10.1039/C3CY00739A
48. [48]
  Chen, W.; Du, W.; Duan, Y.-Z.; Wu, Y.; Yang, S.-Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2007, 46, 7667. doi: 10.1002/anie.200702618
49. [49]
  Ding, D.; Zhao, C.-G. Eur. J. Org. Chem. 2010, 3802. doi: 10.1002/ejoc.201000448
50. [50]
  Cai, Y.-F.; Yang, H.-M.; Li, L.; Jiang, K.-Z.; Lai, G.-Q.; Jiang, J.-X.; Xu, L.-W. Eur. J. Org. Chem. 2010, 4986. doi: 10.1002/chin.201105159
51. [51]
  Zhou, W.; Zhao, J.-G.; Lin, J.; Xu, Y.-X.; Liu, J.; Zhao, S.-J.; Xie, T. J. Hangzhou Normal Univ. (Nat. Sci. Ed.) 2012, 11, 352(in Chinese). doi: 10.3969/j.issn.1674-232X.2012.04.013
52. [52]
  Liu, Y.; Kang, T.-R.; Liu, Q.-Z.; Chen, L.-M.; Wang, Y.-C.; Liu, J.; Xie, Y.-M.; Yang, J.-L.; He, L. Org. Lett. 2013, 15, 6090. doi: 10.1021/ol402977w
53. [53]
  Kang, Y. K.; Kim, D. Y. Adv. Synth. Catal. 2013, 355, 3131. doi: 10.1002/adsc.201300398
54. [54]
  Wang, Y.-Q.; Cui, X.-Y.; Ren, Y.-Y.; Zhang, Y. Org. Biomol. Chem. 2014, 12, 9101. doi: 10.1039/C4OB01902D
55. [55]
  Cui, X.-Y.; Duan, H.-X.; Zhang, Y.; Wang, Y.-Q. Chem. Asian J. 2016, 11, 3118. doi: 10.1002/asia.201601149
56. [56]
  Yalalov, D. A.; Tsogoeva, S. B.; Shubina, T. E.; Martynova, I. M.; Clark, T. Angew. Chem., Int. Ed. 2008, 47, 6624. doi: 10.1002/anie.200800849
57. [57]
  Wang, Y.; Yang, H.; Yu, J.; Miao, Z.; Chen, R. Adv. Synth. Catal. 2009, 351, 3057. doi: 10.1002/adsc.200900597
58. [58]
  Wang, Y.; Yu, J.; Miao, Z.; Chen, R. Org. Biomol. Chem. 2011, 9, 3050. doi: 10.1039/c0ob01268h
59. [59]
  Yang, Q.-C.; Peng, L.; Wang, F.-Y.; Xu, X.-Y.; Wang, L.-X. Chin. J. Synth. Chem. 2013, 21, 237(in Chinese). doi: 10.3969/j.issn.1005-1511.2013.02.028
60. [60]
  Moteki, S. A.; Han, J.; Arimitsu, S.; Akakura, M.; Nakayama, K.; Maruoka, K. Angew. Chem., Int. Ed. 2012, 51, 1187. doi: 10.1002/anie.201107239
61. [61]
  Yang, Q.; Zhang, L.; Ye, C.; Luo, S.; Wu, L.-Z.; Tung, C.-H. Angew. Chem., Int. Ed. 2017, 56, 3694. doi: 10.1002/anie.201700572
62. [62]
  Fu, N.; Li, L.; Yang, Q.; Luo, S. Org. Lett. 2017, 19, 2122. doi: 10.1021/acs.orglett.7b00746
63. [63]
  Lisnyak, V. G.; Lynch-Colameta, T.; Snyder, S. A. Angew. Chem., Int. Ed. 2018, 57, 15162. doi: 10.1002/anie.201809799
1. [1]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
2. [2]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
3. [3]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
4. [4]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
5. [5]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
6. [6]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
7. [7]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
8. [8]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
9. [9]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
10. [10]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
11. [11]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
12. [12]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
13. [13]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
14. [14]
  Shuang Yang , Qun Wang , Caiqin Miao , Ziqi Geng , Xinran Li , Yang Li , Xiaohong Wu . Ideological and Political Education Design for Research-Oriented Experimental Course of Highly Efficient Hydrogen Production from Water Electrolysis in Aerospace Perspective. University Chemistry, 2024, 39(11): 269-277. doi: 10.12461/PKU.DXHX202403044
15. [15]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . S型ZnO/CdIn₂S₄光催化剂制备H₂O₂偶联苄胺氧化的超快电子转移飞秒吸收光谱研究. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-. doi: 10.1016/j.actphy.2025.100064
16. [16]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
17. [17]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
18. [18]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
19. [19]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
20. [20]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004

Get Citation

PDF

XML

Metrics

PDF Downloads(133)
Abstract views(3048)
HTML views(915)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142