Citation: ChenZhang Pengfei, Lan Wenjie, Yu Xuan, Fu Bin. New Application of β, γ-Unsaturated α-Ketoesters in Asymmetric Catalysis[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1448-1460. doi: 10.6023/cjoc202001019 shu

New Application of β, γ-Unsaturated α-Ketoesters in Asymmetric Catalysis

College of Science, China Agricultural University, Beijing 100193

Corresponding author: Fu Bin, fubinchem@cau.edu.cn
Received Date: 13 January 2020
Revised Date: 14 March 2020
Available Online: 31 March 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21572265) and the Ministry of Science and Technology of China (No. 2015BAK45B01)the Ministry of Science and Technology of China 2015BAK45B01the National Natural Science Foundation of China 21572265

Figures(39)

β, γ-Unsaturated α-ketoester is a class of polyfunctional synthon. Due to its 1, 2-dicarbonyl structure and multiple reactive sites, it has been used for the synthesis of various compounds. In the past twenty years, a number of chiral Lewis acid catalysts and organocatalysts have been applied to asymmetric catalytic reactions using β, γ-unsaturated α-ketoesters and various optically active compounds have been synthesized. The current progress of β, γ-unsaturated α-ketoesters in asymmetric catalysis according to the three different reaction sites, unsaturated acyl conjugate system, carbon-carbon double bond and carbonyl group, is summarized. Finally, the limitation of related reactions and the future development trends are also pointed out.
- β, γ-unsaturated α-ketoester,
- asymmetric catalysis,
- application
1. [1]
  Walsh, J. P.; Kozowski, M. C. Fundamentals of Asymmetric Catalysis, Translated by Zhao, Y. J., Chemical Industry Press, Beijing, 2018 (in Chinese).
2. [2]
  Liu, L.; Ma, H.-L.; Xiao, Y.-M.; Du, F.-P.; Qin, Z.-H.; Li, N.; Fu, B. Chem. Commun. 2012, 48, 9281. doi: 10.1039/c2cc34803a
3. [3]
  Liu, Y.; Shang, D. J.; Zhou, X.; Zhu, Y.; Lin, L.-L.; Liu, X.-H.; Feng, X.-M. Org. Lett. 2010, 12, 180. doi: 10.1021/ol902587t
4. [4]
  Peng, L.; Wang, L.-L.; Bai, J.-F.; Jia, L.-N.; Guo, Y.-L; Luo, X.-Y.; Wang, F.-Y.; Yu, X. Y.; Wang, L. X. Org. Biomol. Chem. 2011, 9, 4774. doi: 10.1039/c1ob05607g
5. [5]
  Xu, Z.-H.; Liu, L.; Wheeler, K.; Wang, H. Angew. Chem., Int. Ed. 2011, 50, 3484. doi: 10.1002/anie.201100160
6. [6]
  Eftekhari-Sis, B.; Zirak, M. Chem. Rev. 2015, 115, 151. doi: 10.1021/cr5004216
7. [7]
  Liu, Q.-J.; Wang, L.-J.; Kang, Q.-K.; Zhang, X.-P.; Tang, Y. Angew. Chem., Int. Ed. 2016, 55, 9220. doi: 10.1002/anie.201603911
8. [8]
  Qin, J.-L.; Zhang, Y.-L.; Liu, G.-T.; Zhou, J.; Zhan, R.-T.; Chen, W.-W.; Huang, H. C. Org. Lett. 2019, 21, 7337. doi: 10.1021/acs.orglett.9b02629
9. [9]
  Guo, X.-K.; Liu, G.-F.; An, D.; Zhang, H.; Zhang, S.-Q. Org. Lett. 2019, 21, 5438. doi: 10.1021/acs.orglett.9b01675
10. [10]
  Thirupathi, N.; Wei, F.; Tung, C. H.; Xu, Z.-H. Nat. Commun. 2019, 10, 1. doi: 10.1038/s41467-018-07882-8
11. [11]
  Kano, T.; Maruyama, H.; Homma, C.; Maruoka, K. Chem. Commun. 2018, 54, 3496. doi: 10.1039/C8CC01443D
12. [12]
  Zhang, M.-J.; Wu, Z.-J.; Zhao, J.-Q.; Luo, Y.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W. C. Org. Lett. 2016, 18, 5110. doi: 10.1021/acs.orglett.6b02558
13. [13]
  Yao, Q.; Yu, H.; Zhang, H.; Dong, S.-X.; Chang, F.-Z.; Lin, L.-L.; Liu, X.-H.; Feng, X.-M. Chem. Commun. 2018, 54, 3375. doi: 10.1039/C8CC01040D
14. [14]
  Jin, H.; Lee, J.; Shi, H.; Li, J. Y.; Yoo, E. J.; Song, C. E.; Dyu, D. U. Org. Lett. 2018, 20, 1584. doi: 10.1021/acs.orglett.8b00331
15. [15]
  Wang, L.; Lv, J.; Zhang, L.; Luo, S.-Z. Angew. Chem., Int. Ed. 2017, 56, 10867. doi: 10.1002/anie.201704020
16. [16]
  Li, S.-J.; Lv, J.; Luo, S.-Z. Org. Chem. Front. 2018, 5, 1787. doi: 10.1039/C8QO00319J
17. [17]
  Hao, X. Y.; Lin, L. L.; Tan, F.; Ge, S.-L.; Liu, X.-H.; Feng, X.-M. Org. Chem. Front. 2017, 4, 1647. doi: 10.1039/C7QO00323D
18. [18]
  Ren, H.; Song, X.-Y.; Wang, S. R.; Wang, L.-J.; Tang, Y. Org. Lett. 2018, 20, 3858. doi: 10.1021/acs.orglett.8b01442
19. [19]
  Kostenko, A. A.; Kucherenko, A. S.; Komogortsev, A. N.; Lichitsky, B. V.; Zlotin, S. G. Org. Biomol. Chem. 2018, 16, 9314. doi: 10.1039/C8OB02523A
20. [20]
  Tukhvatshin, R. S.; Kucherenko, A. S.; Nelyubina, Y. V.; Zlotin, S. G. J. Org. Chem. 2019, 84, 13824. doi: 10.1021/acs.joc.9b02021
21. [21]
  Lv, X.-J.; Zhao, W.-W.; Chen, Y.-H.; Wang, S.-B.; Liu, Y. K. Org. Chem. Front. 2019, 6, 1972. doi: 10.1039/C9QO00366E
22. [22]
  Tang, J.; Dong, X.-Y.; Ouyang, W.-L.; Zhu, Y.-L.; Ding, H.-X.; Xiao, Q. Chin. J. Org. Chem. 2019, 39, 2609 (in Chinese).
23. [23]
  Huang, K.-X.; Xie, M.-S.; Zhang, Q.-Y.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2018, 20, 5398. doi: 10.1021/acs.orglett.8b02309
24. [24]
  Xu, J.-X.; Hu, L.-F.; Hu, H.-P.; Ge, S.-L.; Liu, X.-H.; Feng, X.-M. Org. Lett. 2019, 21, 1632. doi: 10.1021/acs.orglett.9b00168
25. [25]
  Wei, R.-B. Spiro Compound Chemistry, Chemical Industry Press, Beijing, 2007 (in Chinese).
26. [26]
  Li, J.; Lin, L.-L.; Hu, B.; Lian, X.; Wang, G.; Liu, X.-H.; Feng, X.-M. Angew. Chem., Int. Ed. 2016, 55, 6075. doi: 10.1002/anie.201601701
27. [27]
  Hu, B.; Li, J.; Gao, W.-D.; Lin, Q. C.; Yang, J.; Lin, L.-L.; Liu, X.-H.; Feng, X.-M. Adv. Synth. Catal. 2018, 360, 2831. doi: 10.1002/adsc.201800576
28. [28]
  Gong, J.; Wan, Q.; Kang, Q. Adv. Synth. Catal. 2018, 360, 4031. doi: 10.1002/adsc.201800492
29. [29]
  Ge, S.-L.; Cao, W.-D.; Kang, T.-F.; Hu, B.; Zhang, H.; Su, Z.-S.; Liu, X.-H.; Feng, X.-M. Angew. Chem., Int. Ed. 2019, 58, 4017. doi: 10.1002/anie.201812842
30. [30]
  Kuang, Y.-L.; Shen, B.; Dai, L.; Yao, Q.; Liu, X.-H.; Lin, L.-L.; Feng, X.-M. Chem. Sci. 2018, 9, 688. doi: 10.1039/C7SC02757E
31. [31]
  Bai, M.; Chen, Y.-Z.; Cui, B.-D.; Xu, X.-Y.; Yuan, W.-C. Tetrahedron 2019, 75, 2155. doi: 10.1016/j.tet.2019.02.036
32. [32]
  Xu, C.-R.; Wang, K.-X.; Li, D. W.; Lin, L.-L.; Feng, X.-M. Angew. Chem., Int. Ed. 2019, 58, 1. doi: 10.1002/anie.201813481
33. [33]
  Cheng, Y.-Y.; Han, Y.-Z.; Li, P.-F. Org. Lett. 2017, 19, 4774. doi: 10.1021/acs.orglett.7b02144
34. [34]
  Li, S.-J.; Lv, J.; Luo, S.-Z. Acta Chim. Sinica 2018, 76, 869 (in Chinese). doi: 10.7503/cjcu20170608
35. [35]
  Cao, J.; Liu, Y.-J.; Zhang, Y.-M.; Wang, Z.-Y.; Xu, P.-F. Org. Chem. Front. 2019, 6, 674.
36. [36]
  Tang, Q.; Fu, K.; Ruan, P.; Dong, S.-X.; Su, Z.-S.; Liu, X.-H.; Feng, X.-M. Angew. Chem., Int. Ed. 2019, 58, 11846. doi: 10.1002/anie.201905533
37. [37]
  Xiong, Q.; Lin, L.-L.; Zhao, Y.-H.; Lang, J.-W.; Liu, X.-H.; Feng, X.-M. J. Org. Chem. 2018, 83, 12527. doi: 10.1021/acs.joc.8b01771
38. [38]
  Zhao, X.-H.; Mei, H.-J.; Xiong, Q.; Fu, K.; Lin, L.-L.; Feng, X.-M. Chem. Commun. 2016, 52, 10692. doi: 10.1039/C6CC05328A
39. [39]
  Zhong, X.-R.; Lv, J.; Luo, S.-Z. Org. Lett. 2017, 19, 3331. doi: 10.1021/acs.orglett.7b01577
40. [40]
  Xie, L.; Yu, X.; Li, J.-Q.; Zhang, Z.-H.; Qin, Z.-H.; Fu, B. Eur. J. Org. Chem. 2017, 3, 657.
41. [41]
  Chen, Y.; Cui. B. D.; Bai, M.; Han, W. Y.; Wan, N. W.; Chen, Y. Z. Tetrahedron 2019, 75, 2971. doi: 10.1016/j.tet.2019.04.040
42. [42]
  Bai, B.; Wang, L.; Yang, J.; Cai, L.-L.; Liu, Q.-J.; Xi, G.-L.; Zhao, Z.-W.; Mao, D.-B.; Chen, Z.-F. Chin. J. Org. Chem. 2019, 39, 1053 (in Chinese).
43. [43]
  Chen, S.-R.; Wang, Y.-M.; Zhou, Z. H. J. Org. Chem. 2016, 81, 11432. doi: 10.1021/acs.joc.6b02070
44. [44]
  Liu, S.-S.; Xu, Z.-H.; Wang, X.; Zhu, H.-R.; Wang, M.-C. J. Org. Chem. 2019, 84, 13881. doi: 10.1021/acs.joc.9b02046
45. [45]
  Zhi, Y.-L.; Huang, J.-H.; Liu, N.; Tao, L.; Dou, X.-W. Org. Lett. 2017, 19, 2378. doi: 10.1021/acs.orglett.7b00909
46. [46]
  Li, P.-F.; Zhao, J.-L.; Li, F.-B.; Chan, A.-S. C.; Kwong, F. Y. Org. Lett. 2010, 12, 5616. doi: 10.1021/ol102254q
47. [47]
  Wei, A.-J.; Nie, J.; Zheng, Y.; Ma, J.-A. J. Org. Chem. 2015, 80, 3766. doi: 10.1021/jo502741z
48. [48]
  Li, P.-F.; Chan, S.-H.; Chan, A. S. C.; Yee, F. Adv. Synth. Catal. 2011, 353, 1179. doi: 10.1002/adsc.201000982
49. [49]
  Luo, W.-W.; Zhao, J.-N.; Ji, J.; Lin, L.-L.; Liu, X.-H.; Mei, H.-J. Chem. Commun. 2015, 51, 10042. doi: 10.1039/C5CC02748A
50. [50]
  Sun, J.-N.; Hu, Y.-B.; Li, Y.-N.; Zhang, S.; Zha, Z.-G.; Wang, Z.-Y. J. Org. Chem. 2017, 82, 5102. doi: 10.1021/acs.joc.7b00159
51. [51]
  Li, Y.-N.; Huang, Y.-K.; Gui, Y.; Sun, J.-N.; Li, J.-D.; Zha, Z.-G.; Wang, Z.-Y. Org. Lett. 2017, 19, 6416. doi: 10.1021/acs.orglett.7b03299
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]
  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
4. [4]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
5. [5]
  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
6. [6]
  Tiantian Zheng , Huiyi Wang , Huimin Li , Xuanhe Liu , Hong Shang . Anti-Counterfeiting National Salvation Chronicle of 006. University Chemistry, 2024, 39(9): 254-258. doi: 10.3866/PKU.DXHX202307032
7. [7]
  Wenli FENG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress on ultralong room temperature phosphorescent carbon dots. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 833-846. doi: 10.11862/CJIC.20240308
8. [8]
  Miaomiao He , Zhiqing Ge , Qiang Zhou , Jiaqing He , Hong Gong , Lingling Li , Pingping Zhu , Wei Shao . Exploring the Fascinating Realm of Quantum Dots. University Chemistry, 2024, 39(6): 231-237. doi: 10.3866/PKU.DXHX202310040
9. [9]
  Laiying Zhang , Yaxian Zhu . Exploring the Silver Family. University Chemistry, 2024, 39(9): 1-4. doi: 10.12461/PKU.DXHX202409015
10. [10]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
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]
  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
13. [13]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
14. [14]
  Lijuan Liu , Xionglei Wang . Preparation of Hydrogels from Waste Thermosetting Unsaturated Polyester Resin by Controllable Catalytic Degradation: A Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 313-318. doi: 10.12461/PKU.DXHX202403060
15. [15]
  Guanghui SUI , Yanyan CHENG . Application of rice husk-based activated carbon-loaded MgO composite for symmetric supercapacitors. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 521-530. doi: 10.11862/CJIC.20240221
16. [16]
  Zhaoxin LI , Ruibo WEI , Min ZHANG , Zefeng WANG , Jing ZHENG , Jianbo LIU . Advancements in the construction of inorganic protocells and their cell mimic and bio-catalytical applications. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2286-2302. doi: 10.11862/CJIC.20240235
17. [17]
  Xueting Cao , Shuangshuang Cha , Ming Gong . 电催化反应中的界面双电层：理论、表征与应用. Acta Physico-Chimica Sinica, 2025, 41(5): 100041-. doi: 10.1016/j.actphy.2024.100041
18. [18]
  Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
19. [19]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
20. [20]
  Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni₃N supported Al-doped SrTiO₃: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371

Get Citation

PDF

XML

Metrics

PDF Downloads(21)
Abstract views(1578)
HTML views(458)

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