Citation: Shan He, Ling Li, Hu Jianfeng, Zhang Hao. Application in the Asymmetric Catalytic Reactions of Chiral Cyclopentadienyl-Transition-Metal Complexes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1548-1556. doi: 10.6023/cjoc201903012 shu

Application in the Asymmetric Catalytic Reactions of Chiral Cyclopentadienyl-Transition-Metal Complexes

Shan He ^a ,
Ling Li ^a ,
Hu Jianfeng ^a ,
Zhang Hao ^a,b,,

a.
College of Chemical & Chemical Engineering, Inner Mongolia University, Hohhot 010021
b.
Inner Mongolia Key Laboratory of Fine Organic Synthesis, Hohhot 010021

Corresponding author: Zhang Hao, haozhang@imu.edu.cn
Received Date: 6 March 2019
Revised Date: 26 April 2019
Available Online: 6 June 2019
Fund Project: the National Natural Science Foundation of China 21861028the Natural Science Foundation of Inner Mongolia 2017MS0206Project supported by the National Natural Science Foundation of China (No.21861028) and the Natural Science Foundation of Inner Mongolia (No. 2017MS0206)

Figures(15)

The chiral Cp ligands as stereocontrolling element of asymmetric catalytic reactions have attracted increasing attention. Particularly, designing and synthesizing more versatile chiral Cp ligands became one of the most interested research focuses in asymmetric catalysis. The complexes of various chiral Cp ligands with different transition metals that advanced in recent years, and the applications of these complexes in catalytic asymmetric reactions are reviewed in this paper.
- cyclopentadienyl ligands,
- asymmetric catalytic reactions,
- transition metal catalysis,
- synthesis
1. [1]
  Togni, A.; Halterman, R. L. In Metallocenes: Synthesis, Reactivity, applications, Vol. 2, Eds.: Jutzi, P.; Edelmann, F. T., Wiley-VCH, New York, 1998, pp. 1~102.
2. [2]
  Halterman, R. L.; Vollhardt, K. P. C. Organometallics 1988, 7, 883. doi: 10.1021/om00094a015
3. [3]
  Halterman, R. L. Chem. Rev. 1992, 92, 965. doi: 10.1021/cr00013a011
4. [4]
  Newton, C. G.; Kossler, D.; Cramer, N. J. Am. Chem. Soc. 2016, 138, 3935. doi: 10.1021/jacs.5b12964
5. [5]
  Ye, B.-H.; Cramer, N. Science 2012, 338, 504. doi: 10.1126/science.1226938
6. [6]
  (a) Jang, H.-J.; Romiti, F.; Torker, S.; Hoveyda, A. H. Nat. Chem. 2017, 9, 1269.
  (b) Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2017, 50, 988.
  (c) Vanable, E. P.; Kennemur, J. L.; Joyce, L. A.; Ruck, R. T.; Schultz, D. M.; Hull, K. L. J. Am. Chem. Soc. 2019, 141, 739.
  (d) Ambler, B. R.; Turnbull, B. W. H.; Suravarapu, S. R.; Uteuliyev, M. M.; Huynh, N. O.; Krische, M. J. J. Am. Chem. Soc. 2018, 140, 9091.
7. [7]
  Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. In Comprehensive Asymmetric Catalysis, Vol. Ⅰ~Ⅲ, Eds.: Brown, J. M.; Buchwald, S. L., Springer-Verlag, New York, 1999, pp. 1~10.
8. [8]
  Wu, P.-L.; Jia, M.-Q.; Lin, W.-L.; Ma, S.-M. Org. Lett. 2018, 20, 554. doi: 10.1021/acs.orglett.7b03637
9. [9]
  (a) Zhu, G.-Q.; Wang, P. Chin. J. Synth. Chem. 2018, 26, 66 (in Chinese).
  (朱广乾, 王鹏, 合成化学, 2018, 26, 66.)
  (b) Inoue, F.; Myuto, K.; Yadav, M. R.; Nakao, Y. Angew. Chem., Int. Ed. 2017, 56, 13307.
  (c) Lin, Z.-Q.; Wang, W.-Z.; Yan, S.-B.; Duan, W.-L. Angew. Chem., Int. Ed. 2015, 54, 6265.
  (d) Wang, Z.-B.; Yin, H.-L.; Fu, G. C. Nature 2018, 563, 379.
  (e) Zheng, S.-C.; Wang, Q.; Zhu, J.-P. Angew. Chem., Int. Ed. 2019, 58, 1494.
  (f) Yao, K.; Yuan, Q.-J.; Qu, X.-X.; Liu, Y.-G.; Liu, D.-L.; Zhang, W.-B. Chem. Sci. 2019, 10, 1767.
10. [10]
  Nishiura, M.; Guo, F.; Hou, Z.-M. Acc. Chem. Res. 2015, 48, 2209.
11. [11]
  Li, S.-H.; Liu, D.-T.; Wang, Z.-C.; Cui, D.-M. ACS Catal. 2018, 8, 6086. doi: 10.1021/acscatal.8b00885
12. [12]
  Zhang, H.; Zhou, B.; Li, H.; Qu, D.-H.; Tian, H. J. Org. Chem. 2013, 78, 2091. doi: 10.1021/jo302107a
13. [13]
  Liu, X.-L.; Li, J.-Z.; Bi, F.-Q.; Zhang, W.-Q.; Gao, Z.-W.; Zhang, G.-F. Eur. J. Inorg. Chem. 2015, 9, 1496.
14. [14]
  Bauer, E. B. Chem. Soc. Rev. 2012, 41, 3153. doi: 10.1039/c2cs15234g
15. [15]
  Matsushima, Y.; Onitsuka, K.; Kondo, T.; Mitsudo, T.; Takahashi, S. J. Am. Chem. Soc. 2001, 123, 10405. doi: 10.1021/ja016334l
16. [16]
  Trost, B. M.; Rao, M.; Dieskau, A. P. J. Am. Chem. Soc. 2013, 135, 18697. doi: 10.1021/ja411310w
17. [17]
  Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429. doi: 10.1021/ja00773a028
18. [18]
  Whitesell, J. K. Chem. Rev. 1989, 89, 1581. doi: 10.1021/cr00097a012
19. [19]
  Ye, B.-H.; Cramer, N. Acc. Chem. Res. 2015, 48, 1308. doi: 10.1021/acs.accounts.5b00092
20. [20]
  Zhang, A.-B.; RajanBabu, T. V. Org. Lett. 2004, 6, 1515. doi: 10.1021/ol0495063
21. [21]
  Li, W.-G.; Zhang, Z.-G.; Xiao, D.-M.; Zhang, X.-M. J. Org. Chem. 2000, 65, 3489. doi: 10.1021/jo000066c
22. [22]
  Ye, B.-H.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 636. doi: 10.1021/ja311956k
23. [23]
  Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139. doi: 10.1021/ja021244h
24. [24]
  Ahmed, I.; Clark, D. A. Org. Lett. 2014, 16, 4332. doi: 10.1021/ol502126r
25. [25]
  Song, G.-Y.; Wylie, W. N. O.; Hou, Z.-M. J. Am. Chem. Soc. 2014, 136, 12209. doi: 10.1021/ja504995f
26. [26]
  Teng, H.-L.; Luo, Y.; Wang, B.-L.; Zhang, L.; Nishiura, M.; Hou, Z.-M. Angew. Chem., Int. Ed. 2016, 55, 15406. doi: 10.1002/anie.v55.49
27. [27]
  Teng, H.-L; Luo, Y.; Nishiura, M.; Hou, Z.-M. J. Am. Chem. Soc. 2017, 139, 16506.
28. [28]
  Dieckmann, M.; Jang, Y.-S.; Cramer, N. Angew. Chem., Int. Ed. 2015, 54, 12149. doi: 10.1002/anie.201506483
29. [29]
  Kossler, D.; Cramer, N. J. Am. Chem. Soc. 2015, 137, 12478. doi: 10.1021/jacs.5b08232
30. [30]
  Hyster, T. K.; Knorr, L.; Ward, T. R.; Rovis, T. Science 2012, 338, 500. doi: 10.1126/science.1226132
31. [31]
  Zheng, J.; Cui, W.-J.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 5242. doi: 10.1021/jacs.6b02302
32. [32]
  (a) Zhu, S.-F.; Yang, Y.; Wang, L.-X.; Liu, B.; Zhou, Q.-L. Org. Lett. 2005, 7, 2333.
  (b) Xie, J.-H.; Wang, L.-X.; Fu, Y.; Zhu, S.-F.; Fan, B.-M.; Duan, H.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2003, 125, 4404.
  (c) Li, S.-Y.; Zhang, J.-W.; Li, X.-L.; Cheng, D.-J.; Tan, B. J. Am. Chem. Soc. 2016, 138, 16561.
33. [33]
  Mei, T.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 5215. doi: 10.1002/anie.v47:28
34. [34]
  Jia, Z.-J.; Merten, C.; Gontla, R.; Daniliuc, C. G.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2017, 56, 2429. doi: 10.1002/anie.201611981
35. [35]
  (a) Potowski, M.; Bauer, J. O.; Strohmann, C.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2012, 51, 9512.
  (b) Potowski, M.; Antonchick, A. P.; Waldmann, H. Chem. Commun. 2013, 49, 7800.
  (c) He, Z.-L.; Teng, H.-L.; Wang, C.-J. Angew. Chem., Int. Ed. 2013, 52, 2934.
36. [36]
  (a) Gotoh, H.; Masui, R.; Ogino, H.; Shoji, M.; Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 6853.
  (b) Gotoh, H.; Ogino, H.; Ishikawa, H.; Hayashi, Y. Tetrahedron 2010, 66, 4894.
37. [37]
  Wang, S.-G.; Park, S. H.; Cramer, N. Angew. Chem. 2018, 130, 5557. doi: 10.1002/ange.v130.19
38. [38]
  Smits, G.; Audic, B.; Wodrich, M. D.; Corminboeuf, C.; Cramer, N. Chem. Sci. 2017, 8, 7174. doi: 10.1039/C7SC02986A
39. [39]
  Audic, B.; Wodrich, M. D.; Cramer, N. Chem. Sci. 2019, 10, 781. doi: 10.1039/C8SC04385J
40. [40]
  Teng, H.-L.; Ma, Y.-H.; Zhan, G.; Nishiura, M.; Hou, Z.-M. ACS Catal. 2018, 8, 4705. doi: 10.1021/acscatal.8b01189
41. [41]
  Ye, B.-H.; Cramer, N. Angew. Chem. 2014, 126, 8030. doi: 10.1002/ange.201404895
42. [42]
  Zheng, J.; Wang, S.-B.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2015, 137, 4880. doi: 10.1021/jacs.5b01707
43. [43]
  Chidipudi, S. R.; Burns, D. J.; Khan, I.; Lam, H. W. Angew. Chem., Int. Ed. 2015, 54, 13975. doi: 10.1002/anie.201507029
44. [44]
  Jang, Y.-S.; Dieckmann, M.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 15088. doi: 10.1002/anie.201708440
45. [45]
  Kossler, D.; Perrin, F. G.; Suleymanov, A. A.; Kiefer, G.; Scopelliti, R.; Severin, K.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 11490. doi: 10.1002/anie.v56.38
46. [46]
  Zheng, J.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 13244. doi: 10.1002/anie.201408805
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  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
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
5. [5]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
6. [6]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
7. [7]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
8. [8]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
9. [9]
  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
10. [10]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
11. [11]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
12. [12]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
17. [17]
  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
18. [18]
  Lu Zhuoran , Li Shengkai , Lu Yuxuan , Wang Shuangyin , Zou Yuqin . Cleavage of C―C Bonds for Biomass Upgrading on Transition Metal Electrocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2306003-0. doi: 10.3866/PKU.WHXB202306003
19. [19]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(1262)
HTML views(220)

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