Citation: Liu Yaozong, Xu Pengfei, Ma Jianjun, Li Xiaoming, Liang Ruiyuan, Teng Zhijun. Bifunctional Thioureas Catalyzed Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β, γ-Unsaturated α-Keto Esters[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1378-1383. doi: 10.6023/cjoc201911027 shu

Bifunctional Thioureas Catalyzed Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β, γ-Unsaturated α-Keto Esters

a.
Gansu Yinguang Juyin Chemical Co., Ltd., Baiyin, Gansu 730900
b.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000

Corresponding author: Liu Yaozong,
Received Date: 23 November 2019
Revised Date: 4 January 2020
Available Online: 15 January 2020

Figures(2)

The asymmetric Michael addition of 1-acetylindolin-3-ones to β, γ-unsaturated α-keto esters catalyzed by bifunctional thioureas has been developed. Enantio-pure 2-substituted indolin-3-one derivatives were obtained easily in excellent yields (up to 99%) with good diastereoselectivity (up to 10:1) and excellent enantioselectivities (up to 99.5%), which would be useful for the chiral synthesis of indole-related compounds.
- asymmetric catalysis,
- bifunctional thiourea,
- Michael addition,
- 1-acetylindolin-3-one,
- β, γ-unsaturated α-keto ester
1. [1]
2. [2]
3. [3]
  (a) Zhou, L.; Lin, L.-L.; Wang, W.-T.; Ji, J.; Liu, X.-H.; Feng, X.-M. Chem. Commun. 2010, 46, 3601.
  (b) Herrera, R. P.; Monge, D.; Zamora, E. M.; Fernández, R.; Lassaletta, J. M. Org. Lett. 2007, 11, 3303.
  (c) Liu, S.-S.; Xu, Z.-H.; Wang, X.; Zhu, H.-R.; Wang, M.-C. J. Org. Chem. 2019, 84, 13881.
  (d) Zhang, M.-L.; Wu, Z.-J.; Zhao, J.-Q.; Luo, Y.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2016, 18, 5110.
  (e) Zhi, Y.-L.; Huang, J.-H.; Liu, N.; Lu, T.; Dou, X.-W. Org. Lett. 2017, 19, 2378.
4. [4]
5. [5]
  (a) Baran, P. S.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 7904.
  (b) Karadeolian, A.; Kerr, M. A. Angew. Chem., Int. Ed. 2010, 49, 1133.
  (c) Higuchi, K.; Sato, Y.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Org. Lett. 2009, 11, 197.
6. [6]
  (a) Witkop, B. J. Am. Chem. Soc. 1950, 72, 614.
  (b) Lednicer, D. L.; Emmert, D. E. J. Heterocycl. Chem. 1970, 7, 575.
  (c) Liu, Y.; McWhorter, W. W. J. Org. Chem. 2003, 68, 2618.
  (d) Buller, M. J.; Cook, T. G.; Kobayashi, Y. Heterocycles 2007, 72, 163.
  (e) Higuchi, K.; Sato, Y.; Kojima, S.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Tetrahedron 2010, 66, 1236.
7. [7]
  a) Higuchi, K.; Masuda, K.; Koseki, T.; Hatori, M.; Sakamoto, M.; Kawasaki, T. Heterocycles 2007, 73, 641.
  (b) Yin, Q.; You, S.-L. Chem. Sci. 2011, 2, 1344.
  (c) Sun, W.-S.; Hong, L.; Wang, R. Chem.-Eur. J. 2011, 17, 6030.
  (d) Rueping, M.; Raja, S.; Nunez, A. Adv. Synth. Catal. 2011, 353, 563.
  (e) Liu, Y.-Z.; Cheng, R.-L.; Xu, P.-F. J. Org. Chem. 2011, 76, 2884.
  (f) Liu, Y.-Z.; Zhang, J.; Xu, P.-F.; Luo, Y.-C. J. Org. Chem. 2011, 76, 7551.
  (g) Jin, C.-Y.; Wang, Y.; Liu, Y.-Z.; Shen, C.; Xu, P.-F. J. Org. Chem. 2012, 77, 11307.
  (f) Zhao, Y.-L.; Wang, Y.; Cao, J.; Liang, Y.-M.; Xu, P.-F. Org. lett. 2014, 16, 2438.
  (g) Chen, S.-R.; Wang, Y.-M.; Zhou, Z.-H. J. Org. Chem. 2016, 81, 11432.
8. [8]
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]
  Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253
3. [3]
  Ya-Ling Li , Jia-Wei Ke , Yue Liu , Dong-Mei Yao , Jing-Dong Zhang , You-Cai Xiao , Fen-Er Chen . Asymmetric conjugated addition of aryl Grignard reagents for the construction of chromanones bearing quaternary stereogenic centers in batch and flow. Chinese Chemical Letters, 2025, 36(6): 110377-. doi: 10.1016/j.cclet.2024.110377
4. [4]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
5. [5]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
6. [6]
  Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
7. [7]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
8. [8]
  Shicheng Dong , Jun Zhu . Could π-aromaticity cross an unsaturated system to a fully saturated one?. Chinese Chemical Letters, 2024, 35(6): 109214-. doi: 10.1016/j.cclet.2023.109214
9. [9]
  Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
10. [10]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
11. [11]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277
12. [12]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
13. [13]
  Jinli Chen , Shouquan Feng , Tianqi Yu , Yongjin Zou , Huan Wen , Shibin Yin . Modulating Metal-Support Interaction Between Pt3Ni and Unsaturated WOx to Selectively Regulate the ORR Performance. Chinese Journal of Structural Chemistry, 2023, 42(10): 100168-100168. doi: 10.1016/j.cjsc.2023.100168
14. [14]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
15. [15]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
16. [16]
  Qiang Feng , Jindong Hao , Ya Hu , Rong Fu , Wei Wei , Dong Yi . Photocatalytic multi-component synthesis of ester-containing quinoxalin-2(1H)-ones using water as the hydrogen donor. Chinese Chemical Letters, 2025, 36(6): 110582-. doi: 10.1016/j.cclet.2024.110582
17. [17]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
18. [18]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
19. [19]
  Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
20. [20]
  Juhong Zhou , Hui Zhao , Ping Han , Ziyue Wang , Yan Zhang , Xiaoxia Mao , Konglin Wu , Shengjue Deng , Wenxiang He , Binbin Jiang . Strategic modulation of CoFe sites for advanced bifunctional oxygen electrocatalyst. Chinese Journal of Structural Chemistry, 2025, 44(1): 100470-100470. doi: 10.1016/j.cjsc.2024.100470

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1100)
HTML views(164)

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