Citation: Ge Xin, Chen Xinzhi, Qian Chao. Progress on the Lewis-Basic Organocatalytic Asymmetric Reduction of Imines[J]. Chinese Journal of Organic Chemistry, ;2016, 36(6): 1208-1217. doi: 10.6023/cjoc201512029 shu

Progress on the Lewis-Basic Organocatalytic Asymmetric Reduction of Imines

Ge Xin ^a,b ,
Chen Xinzhi ^b ,
Qian Chao ^b,*,,

a.
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122
b.
Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University, Hangzhou 310027

Corresponding author: Qian Chao, qianchao@zju.edu.cn
Received Date: 21 December 2015
Revised Date: 26 January 2016

Fund Project: Zhejiang Provincial Public Technology Research of China Nos.2014C31123,2015C31038and the Fundamental Research Funds for the Central Universities No.JUSRP115A05Project supported by the Natural Science Foundation of China Nos.21376213,21476194

Figures(9)

Recently, the asymmetric reduction of imines catalyzed by Lewis-basic organocatalyst has been received much attention as the cheap hydrogen source and the simple post treatment. Based on the different functional groups of organocatalysts, this paper introduced formamide, pyridine amide, sulfonamide, supported and other Lewis basic organocatalysts. The structural characteristics, catalytic activity and mechanism of the Lewis-basic organocatalysts were summarized.
- imine,
- Lewis-base,
- organocatalyst,
- asymmetric reduction
1. [1]
2. [2]
  Blaser, H. U. Chem Commun. 2003, 293.
3. [3]
  Langlois, N.; Dang, T.; Kagan, H. B. Tetrahedron Lett. 1973, 4865.
4. [4]
  Bakos, J.; Orosz, A.; Heil, B.; Laghmari, M.; Lhoste, P.; Sinou, D. J. Chem.Soc.-Chem. Commun. 1991, 1684.
5. [5]
6. [6]
  Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1992, 114, 7562.
7. [7]
  Schnider, P.; Koch, G.; Pretot, R.; Wang, G. Z.; Bohnen, F. M.; Kruger, C.; Pfaltz, A. Chem-Eur J. 1997, 3, 887.
8. [8]
  Xiao, D. M.; Zhang, X. M. Angew. Chem., Int. Ed. 2001, 40, 3425.
9. [9]
  Wang, C.; Villa-Marcos, B.; Xiao, J. L. Chem. Commun. 2011, 47, 9773.
10. [10]
  Blaser, H. U.; Buser, H. P.; Coers, K.; Hanreich, R.; Jalett, H. P.; Jelsch, E.; Pugin, B.; Schneider, H. D.; Spindler, F.; Wegmann, A. Chimia 1999, 53, 275.
11. [11]
  Blaser, H. U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103.
12. [12]
  List, B. J. Am. Chem. Soc. 2000, 122, 9336.
13. [13]
  List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395.
14. [14]
  List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573.
15. [15]
  Mitsumori, S.; Zhang, H.; Cheong, P. H. Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F. J. Am. Chem. Soc. 2006, 128, 1040.
16. [16]
  List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
17. [17]
  Iwasaki, F.; Onomura, O.; Mishima, K.; Kanematsu, T.; Maki, T.; Matsumura, Y. Tetrahedron Lett. 2001, 42, 2525.
18. [18]
  Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int Ed. 2005, 44, 7424.
19. [19]
  Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 6751.
20. [20]
  Rueping, M.; Antonchick, A. R.; Theissmann, T. Angew Chem., Int. Ed. 2006, 45, 3683.
21. [21]
  Rueping, M.; Theissmann, T.; Antonchick, A. P. Synlett 2006, 1071.
22. [22]
  Malkov, A. V.; Mariani, A.; MacDougall, K. N.; Kocovsky, P. Org. Lett. 2004, 6, 2253.
23. [23]
  Wang, Z. Y.; Wei, S. Y.; Wang, C.; Sun, J. Tetrahedron: Asymmetry 2007, 18, 705.
24. [24]
  Wang, Z. Y.; Wang, C.; Zhou, L.; Sun, J. Org. Biomol. Chem. 2013, 11, 787.
25. [25]
  Wang, Z. Y.; Cheng, M.; Wu, P. C.; Wei, S. Y.; Sun, J. Org. Lett. 2006, 8, 3045.
26. [26]
  Wang, Z. Y.; Ye, X. X.; Wei, S. Y.; Wu, P. C.; Zhang, A. J.; Sun, J. Org. Lett. 2006, 8, 999.
27. [27]
  Zhou, L.; Wang, Z. Y.; Wei, S. Y.; Sun, J. Chem. Commun. 2007, 2977.
28. [28]
  Zhang, Z. G.; Rooshenas, P.; Hausmann, H.; Schreiner, P. R. Synthesis-Stuttgart 2009, 1531.
29. [29]
  Kanemitsu, T.; Umehara, A.; Haneji, R.; Nagata, K.; Itoh, T. Tetrahedron 2012, 68, 3893.
30. [30]
  Malkov, A. V.; Stoncius, S.; MacDougall, K. N.; Mariani, A.; McGeoch, G. D.; Kocovsky, P. Tetrahedron 2006, 62, 264.
31. [31]
  Malkov, A. V.; Vrankova, K.; Sigerson, R. C.; Stoncius, S.; Kocovsky, P. Tetrahedron 2009, 65, 9481.
32. [32]
  Malkov, A. V.; Vrankova, K.; Stoncius, S.; Kocovsky, P. J. Org. Chem. 2009, 74, 5839.
33. [33]
  Malkov, A. V.; Stoncius, S.; Kocovsky, P. Angew. Chem., Int Ed. 2007, 46, 3722.
34. [34]
  Malkov, A. V.; Stoncius, S.; Vrankova, K.; Arndt, M.; Kocovsky, P. Chem. Eur. J. 2008, 14, 8082.
35. [35]
  Xiao, Y.-C.; Wang, C.; Yao, Y.; Sun, J.; Chen, Y.-C. Angew. Chem., Int. Ed. 2011, 50, 10661.
36. [36]
  Onomura, O.; Kouchi, Y.; Iwasaki, F.; Matsumura, Y. Tetrahedron Lett. 2006, 47, 3751.
37. [37]
  Zheng, H.-J.; Chen, W.-B.; Wu, Z.-J.; Deng, J.-G.; Lin, W.-Q.; Yuan, W.-C.; Zhang, X.-M. Chem-Eur J. 2008, 14, 9864.
38. [38]
  Xue, Z.-Y.; Jiang, Y.; Yuan, W.-C.; Zhang, X.-M. Eur. J. Org. Chem. 2010, 616.
39. [39]
  Chen, X.; Zheng, Y.; Shu, C.; Yuan, W.; Liu, B.; Zhang, X. J. Org. Chem. 2011, 76, 9109.
40. [40]
  Gautier, F. M.; Jones, S.; Martin, S. J. Org. Biomol. Chem. 2009, 7, 229.
41. [41]
  Jones, S.; Li, X. F. Tetrahedron 2012, 68, 5522.
42. [42]
  Zheng, H.; Deng, J.; Lin, W.; Zhang, X. Tetrahedron Lett. 2007, 48, 7934.
43. [43]
  Xue, Z.-Y.; Jiang, Y.; Peng, X.-Z.; Yuan, W.-C.; Zhang, X.-M. Adv. Synth. Catal. 2010, 352, 2132.
44. [44]
  Jiang, Y.; Chen, X.; Zheng, Y.; Xue, Z.; Shu, C.; Yuan, W.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 7304.
45. [45]
  Guizzetti, S.; Benaglia, M.; Bonsignore, M.; Raimondi, L. Org. Biomol. Chem. 2011, 9, 739.
46. [46]
  Pei, D.; Wang, Z.; Wei, S.; Zhang, Y.; Sun, J. Org. Lett. 2006, 8, 5913.
47. [47]
  Pei, D.; Zhang, Y.; Wei, S. Y.; Wang, M.; Sun, J. Adv. Synth. Catal. 2008, 350, 619.
48. [48]
  Wang, C.; Wu, X.; Zhou, L.; Sun, J. Chem. Eur. J. 2008, 14, 8789.
49. [49]
  Wu, X. J.; Li, Y.; Wang, C.; Zhou, L.; Lu, X. X.; Sun, J. A. Chem. Eur. J. 2011, 17, 2846.
50. [50]
  Malkov, A. V.; Liddon, A.; Ramirez-Lopez, P.; Bendova, L.; Haigh, D.; Kocovsky, P. Angew Chem., Int. Edit .2006, 45, 1432.
51. [51]
52. [52]
  Ge, X.; Qian, C.; Chen, Y. B.; Chen, X. Z. Tetrahedron: Asymmetry 2014, 25, 596.
53. [53]
  Malkov, A. V.; Figlus, M.; Stoncius, S.; Kocovsky, P. J. Org. Chem. 2007, 72, 1315.
54. [54]
  Malkov, A. V.; Figlus, M.; Kocovsky, P. J. Org. Chem. 2008, 73, 3985.
55. [55]
  Malkov, A. V.; Figlus, M.; Cooke, G.; Caldwell, S. T.; Rabani, G.; Prestly, M. R.; Kocovsky, P. Org. Biomol. Chem. 2009, 7, 1878.
56. [56]
  Malkov, A. V.; Figlus, M.; Prestly, M. R.; Rabani, G.; Cooke, G.; Kocovsky, P. Chem. Eur. J. 2009, 15, 9651.
57. [57]
  Ge, X.; Qian, C.; Chen, X. Z. Tetrahedron: Asymmetry 2014, 25, 1450.
58. [58]
59. [59]
  Ge, X.; Qian, C.; Ye, X. M.; Chen, X. Z. RSC Adv. 2015, 5, 65402.
1. [1]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
7. [7]
  Haiping Wang . A Streamlined Method for Drawing Lewis Structures Using the Valence State of Outer Atoms. University Chemistry, 2024, 39(8): 383-388. doi: 10.12461/PKU.DXHX202401073
8. [8]
  Mengxiu Li , Jiahui Mao , Jiangfeng Ni , Liang Li . Three birds with one stone: modification of Li₅FeO₄ with thermal induction of Lewis acid. Acta Physico-Chimica Sinica, 2026, 42(4): 100189-0. doi: 10.1016/j.actphy.2025.100189
9. [9]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
10. [10]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
11. [11]
  Mian Wei , Chang Cheng , Bowen He , Bei Cheng , Kezhen Qi , Chuanbiao Bie . Inorganic-organic CdS/YBTPy S-scheme photocatalyst for efficient hydrogen production and its mechanism. Acta Physico-Chimica Sinica, 2025, 41(12): 100158-0. doi: 10.1016/j.actphy.2025.100158
12. [12]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 100027-0. doi: 10.3866/PKU.WHXB202406007
13. [13]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . Performance and Electrochemical Asymmetry Optimization of Hydrogen Electrode Supported Reversible Solid Oxide Cell. Acta Physico-Chimica Sinica, 2025, 41(1): 100005-0. doi: 10.3866/PKU.WHXB202309037
14. [14]
  Guoqiang Peng , Xiuyan Li , Min Li , Zhibo Su , Falu Hu , Guowei Zhou . Engineering efficient metal-organic frameworks for photocatalytic CO₂ reduction. Acta Physico-Chimica Sinica, 2026, 42(2): 100164-0. doi: 10.1016/j.actphy.2025.100164
15. [15]
  Jingping Li , Suding Yan , Jiaxi Wu , Qiang Cheng , Kai Wang . Improving hydrogen peroxide photosynthesis over inorganic/organic S-scheme photocatalyst with LiFePO₄. Acta Physico-Chimica Sinica, 2025, 41(9): 100104-0. doi: 10.1016/j.actphy.2025.100104
16. [16]
  Wenjun Zhu , Chenbin Ai , Kaiqiang Xu , Yatai Zhou , Xidong Zhang , Yong Zhang . WO₃@TP inorganic@organic S-scheme photocatalyst for boosting H₂O₂ production. Acta Physico-Chimica Sinica, 2026, 42(3): 100184-0. doi: 10.1016/j.actphy.2025.100184
17. [17]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026
18. [18]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
19. [19]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
20. [20]
  Xueting Feng , Ziang Shang , Rong Qin , Yunhu Han . Advances in Single-Atom Catalysts for Electrocatalytic CO₂ Reduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2305005-0. doi: 10.3866/PKU.WHXB202305005

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2289)
HTML views(495)

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