Citation: Tan Fen, Xiao Wenjing, Zeng Guoping. Recent Advances in 3-Isothiocyanato Oxindoles Engaged Asymmetric Cascade Reactions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 824-840. doi: 10.6023/cjoc201611017 shu

Recent Advances in 3-Isothiocyanato Oxindoles Engaged Asymmetric Cascade Reactions

Tan Fen ^a,b,*,, ,
Xiao Wenjing ^b ,
Zeng Guoping ^a

a.
Hubei Key Laboratory of Purification and Application of Plant Anti-cancer Active Ingredients, Hubei University of Education, Wuhan 430205
b.
Key Laboratory of Pesticide & Chemical Biology Ministry of Education and College of Chemistry, Central China Normal University, Wuhan 430079

Corresponding author: Tan Fen, tanfen@hue.edu.cn
Received Date: 15 November 2016
Revised Date: 21 December 2016

Fund Project: the National Natural Science Foundation of China 21602052the Scientific Research Project of Hubei Provincial Department of Education Q20163004

Figures(17)

3-Isothiocyanato oxindoles have been widely employed as a class of highly reactive and novel reagents in the enantioselective synthesis of diverse spirooxindoles. This review summarizes the recent advances of 3-isothiocyanato oxindoles mediated some types of cascade process in the past six years, including properties of reaction, activation models and synthetic applications. Furthermore, the prospects of this concept are also discussed.
- 3-isothiocyanato oxindole,
- spirooxindole,
- asymmetric synthesis,
- cascade reaction
1. [1]
  Lin, H.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 36. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209.
3. [3]
  (a) Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381.
  (b) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156.
  (c) Rios, R. Chem. Soc. Rev. 2012, 41, 1060.
  (d) Cheng, D.-J.; Ishihara, Y.; Tan, B.; Barbas Ⅲ, C. F. ACS Catal. 2014, 4, 743.
  (e) Xiao, Y.-L.; Zhou, Y.; Wang, J.; Wang, J.-X.; Liu, H. Chin. J. Org. Chem. 2015, 35, 2035 (in Chinese). (肖永龙, 周宇, 王江, 王进欣, 柳红, 有机化学, 2015, 35, 2035.
4. [4]
  Suchy, M.; Kutschy, P.; Monde, K. J. Org. Chem. 2001, 66, 3940. doi: 10.1021/jo0155052
5. [5]
  (a) Cui, C. B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 832.
  (b) Edmondson, S.; Danishefsky, S.-J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.
  (c) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. J. Am. Chem. Soc. 2005, 127, 10130.
  (d) Cheng, M.-N.; Wang, H.; Gong, L.-Z. Org. Lett. 2011, 13, 2418.
6. [6]
  Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527. doi: 10.1021/jo00023a016
7. [7]
  (a) Potawel, S. E.; Mehta, U. K.; Waseem, S.; Dhalawat, H. J.; Lunya, K. P.; Mantri, R. A.; Vetol, Y. D. Pharmacology 2008, 2, 197.
  (b) Litvinov, Y. M.; Mortikov, V. Y.; Shestopalov, A. M. J. Comb. Chem. 2008, 10, 741.
8. [8]
  Rottmann, M.; McNamara, C.; Yeung, B. K. S.; Lee, M. C. S.; Zou, B.; Russell, B.; Seitz, P.; Plouffe, D. M.; Dharia, N. V.; Tan, J.; Cohen, S. B.; Spencer, K. R.; González-Páez, G. E.; Lakshminarayana, S. B.; Goh, A.; Suwanarusk, R.; Jegla, T.; Schmitt, E. K.; Beck, H. P.; Brun, R.; Nosten, F.; Renia, L.; Dartois, V.; Keller, T. H.; Fidock, D. A.; Winzeler, E. A.; Diagana, T. T. Science 2010, 329, 1175. doi: 10.1126/science.1193225
9. [9]
  Liang, H.; Li, R.-M.; Yuan, Q.-P. J. Beijing Univ. Chem. Technol. (Nat. Sci.) 2015, 42, 1 (in Chinese).
10. [10]
  (a) Chen, W.-B.; Wu, Z.-J.; Hu, J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2011, 13, 2472.
  (b) Han, W.-Y.; Zhao, J.-Q.; Zuo, J.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal. 2015, 357, 3007.
11. [11]
  Jiang, K.; Jia, Z.-J.; Yin, X.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 2766. doi: 10.1021/ol100857s
12. [12]
  Han, Y.-Y.; Chen, W.-B.; Han, W.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2012, 14, 490. doi: 10.1021/ol203081x
13. [13]
  Kayal, S.; Mukherjee, S. Org. Lett. 2015, 17, 5508. doi: 10.1021/acs.orglett.5b02929
14. [14]
  Chen, W.-B.; Han, W.-Y.; Han, Y.-Y.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2013, 69, 5281. doi: 10.1016/j.tet.2013.05.002
15. [15]
  (a) Kato, S.; Kanai, M.; Matsunaga, S. Chem. Asian J. 2013, 8, 1768.
  (b) Kato, S.; Kanai, M.; Matsunaga, S. Heterocycles 2014, 88, 475.
16. [16]
  Kato, S.; Yoshino, T.; Shibasaki, M.; Kanai, M.; Matsunaga, S. Angew. Chem., Int. Ed. 2012, 51, 7007. doi: 10.1002/anie.201203005
17. [17]
  (a) Vassilev, L. T.; Vu, B. T.; Graves, B.; Carvajal, D.; Podlaski, F.; Filipovic, Z.; Kong, N.; Kammlott, U.; Lukacs, C.; Klein, C.; Fotouhi, N.; Liu, E. A. Science 2004, 303, 844.
  (b) Tovar, C.; Rosinski, J.; Filipovic, Z.; Higgins, B.; Kolinsky, K.; Hilton, H.; Zhao, X.; Vu, B. T.; Qing, W.; Packman, K.; Myklebost, O.; Heimbrook, D. C.; Vassilev, L. T. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 1888.
18. [18]
  Shangary, S.; Qin, D.; McEachern, D.; Liu, M.; Miller, R. S.; Qiu, S.; Nikolovska-Coleska, Z.; Ding, K.; Wang, G.; Chen, J.; Bernard, D.; Zhang, J.; Lu, Y.; Gu, Q.; Shah, R. B.; Pienta, K. J.; Ling, X.; Kang, S.; Guo, M.; Sun, Y.; Yang, D.; Wang, S. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 3933. doi: 10.1073/pnas.0708917105
19. [19]
  Cai, H.; Zhou, Y.; Zhang, D.; Xu, J.-Y.; Liu, H. Chem. Commun. 2014, 50, 14771. doi: 10.1039/C4CC06000H
20. [20]
  Bai, M.; Cui, B.-D.; Zuo, J.; Zhao, J.-Q.; You, Y.; Chen, Y.-Z.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2015, 71, 949. doi: 10.1016/j.tet.2014.12.074
21. [21]
  Du, D.; Xu, Q.; Li, X.-G.; Shi, M. Chem. Eur. J. 2016, 22, 4733. doi: 10.1002/chem.v22.14
22. [22]
  Cao, Y.-M.; Shen, F.-F.; Zhang, F.-T.; Wang, R. Chem. Eur. J. 2013, 19, 1184. doi: 10.1002/chem.201204114
23. [23]
  Wu, H.; Zhang, L.-L.; Tian, Z.-Q.; Huang, Y.-D.; Wang, Y.-M. Chem. Eur. J. 2013, 19, 1747. doi: 10.1002/chem.201203221
24. [24]
  Tan, F.; Cheng, H.-G.; Feng, B.; Zou, Y.-Q.; Duan, S.-W.; Chen, J.-R.; Xiao, W.-J. Eur. J. Org. Chem. 2013, 2071.
25. [25]
  Wu, S.; Zhu, X.-L.; He, W.-J.; Wang, R.-M.; Xie, X.-H.; Qin, D.-B.; Jing, L.-H.; Chen, Z.-Q. Tetrahedron 2013, 69, 11084. doi: 10.1016/j.tet.2013.11.016
26. [26]
  Tan, F.; Lu, L.-Q.; Yang, Q.-Q.; Guo, W.; Bian, Q.; Chen, J.-R.; Xiao, W.-J. Chem. Eur. J. 2014, 20, 3415. doi: 10.1002/chem.v20.12
27. [27]
  Fu, Z.-K.; Pan, J.-Y.; Xu, D.-C.; Xie, J.-W. RSC Adv. 2014, 4, 51548. doi: 10.1039/C4RA07860H
28. [28]
  Kayal, S.; Mukherjee, S. Eur. J. Org. Chem. 2014, 6696.
29. [29]
  (a) Zhao, J.-Q.; Zhou, M.-Q.; Wu, Z.-J.; Wang, Z.-H.; Yue, D.-F.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2015, 17, 2238.
  (b) Zhao, J.-Q.; Wu, Z.-J.; Zhou, M.-Q.; Xu, X.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2015, 17, 5020.
30. [30]
  Du, D.; Jiang, Y.; Xu, Q.; Shi, M. Adv. Synth. Catal. 2013, 355, 2249. doi: 10.1002/adsc.201300460
31. [31]
  Wang, L.-Q.; Yang, D.-X.; Li, D.; Liu, X.-H.; Zhao, Q.; Zhu, R.-R.; Zhang, B.-Z.; Wang, R. Org. Lett. 2015, 17, 4260. doi: 10.1021/acs.orglett.5b02052
32. [32]
  Du, D.; Jiang, Y.; Xu, Q.; Tang, X.-Y.; Shi, M. ChemCatChem 2015, 7, 1366. doi: 10.1002/cctc.201500141
33. [33]
  Chowdhury, R.; Kumar, M.; Ghosh, S. K. Org. Biomol. Chem. 2016, 14, 11250. doi: 10.1039/C6OB02104B
34. [34]
  Liu, X.-L.; Han, W.-Y.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2013, 15, 1246. doi: 10.1021/ol400183k
35. [35]
  Han, W.-Y.; Li, S.-W.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Chem. Eur. J. 2013, 19, 5551. doi: 10.1002/chem.v19.18
36. [36]
  Chen, Q.; Liang, J.-Y.; Wang, S.-L.; Wang, D.; Wang, R. Chem. Commun. 2013, 49, 1657. doi: 10.1039/c3cc38386e
37. [37]
  Cui, B.-D.; Li, S.-W.; Zuo, J.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron 2014, 70, 1895. doi: 10.1016/j.tet.2014.01.036
38. [38]
  Zhao, H.-W.; Tian, T.; Pang, H.-L.; Li, B.; Chen, X.-Q.; Yang, Z.; Meng, W.; Song, X.-Q.; Zhao, Y.-D.; Liu, Y.-Y. Adv. Synth. Catal. 2016, 358, 2619. doi: 10.1002/adsc.v358.16
39. [39]
  Kayal, S.; Mukherjee, S. Org. Biomol. Chem. 2016, 14, 10175. doi: 10.1039/C6OB02187E
40. [40]
  Liu, L.; Zhao, B.-L.; Du, D.-M. Eur. J. Org. Chem. 2016, 4711.
41. [41]
  Jiang, Y.; Pei, C.-K.; Du, D.; Li, X.-G.; He, Y.-N.; Xu, Q.; Shi, M. Eur. J. Org. Chem. 2013, 7895.
42. [42]
  Wang, L.-Q.; Yang, D.-X.; Li, D.; Wang, R. Org. Lett. 2015, 17, 3004. doi: 10.1021/acs.orglett.5b01291
43. [43]
  Zhu, G.-M.; Sun, W.-S.; Wu, C.-Y.; Li, G.-F.; Hong, L.; Wang, R. Org. Lett. 2013, 15, 4988. doi: 10.1021/ol402295m
1. [1]
  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
2. [2]
  Xincan Zhou , Xueyao Wang , Xiaokang Chen , Di Lan , Yuting Gao , Xiaoxia Wang , Daohao Li , Shuchao Zhang , Lijie Zhang , Guanglei Wu . Charge redistribution on Pd mediated by electronically asymmetric carbon for boosting ethanol oxidation. Acta Physico-Chimica Sinica, 2026, 42(7): 100287-0. doi: 10.1016/j.actphy.2026.100287
3. [3]
  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
4. [4]
  Dengke Ma . Application of Integrating Fundamental Knowledge and Cutting-Edge Developments in the Teaching of Organic Synthesis: Taking the Asymmetric Meinwald Rearrangement as an Example. University Chemistry, 2026, 41(4): 67-74. doi: 10.12461/PKU.DXHX202502112
5. [5]
  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
6. [6]
  Shaohua Wu , Jianfeng Yan , Chunfa Xu , Yuanming Li , Kai Yang , Caixia Lin . Construction of the synthetic chemistry experiment course under the Chemistry “101 Plan”: instructional design and implementation of the L-proline-catalyzed asymmetric aldol condensation reaction experiment. University Chemistry, 2026, 41(6): 152-159. doi: 10.12461/PKU.DXHX202511100
7. [7]
  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
8. [8]
  Fengcheng Jia , Zixia Zheng , Fei Li , Huiqin Duan , Gang Wang . 串联S_NAr/Aldol缩合构建季碳稠合吲哚啉. University Chemistry, 2026, 41(5): 190-197. doi: 10.12461/PKU.DXHX202511104
9. [9]
  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
10. [10]
  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
11. [11]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-0. doi: 10.3866/PKU.WHXB202408015
12. [12]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
13. [13]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
14. [14]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
15. [15]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
16. [16]
  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
17. [17]
  Kangjuan Cheng , Chunxiao Liu , Youpeng Wang , Qiu Jiang , Tingting Zheng , Xu Li , Chuan Xia . Design of noble metal catalysts and reactors for the electrosynthesis of hydrogen peroxide. Acta Physico-Chimica Sinica, 2025, 41(10): 100112-0. doi: 10.1016/j.actphy.2025.100112
18. [18]
  Tao Wen , Tao Zhang , Changguo Sun , Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055
19. [19]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
20. [20]
  Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(3261)
HTML views(661)

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