SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 5: 1378 - 1383

DOI: https://doi.org/10.6023/cjoc201911027

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

  • Liu Yaozong ,
  • Xu Pengfei ,
  • Ma Jianjun ,
  • Li Xiaoming ,
  • Liang Ruiyuan ,
  • Teng Zhijun
Expand
  • 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

Received date: 2019-11-23

  Revised date: 2020-01-04

  Online published: 2020-01-15

Fold

Abstract

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.

Key words： asymmetric catalysis; bifunctional thiourea; Michael addition; 1-acetylindolin-3-one; β,γ-unsaturated α-keto ester

Cite this article

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

References

[1] (a) Harutyunyan, S. R.; Hartog, T. D.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824.
(b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
(c) Li, N.; Xi, G.-H.; Wu, Q.-H.; Liu, W.-H.; Ma, J.-J.; Wang, C. Chin. J. Org. Chem. 2009, 29, 1018(in Chinese). (李宁, 郗国宏, 吴秋华, 刘伟华, 马晶军, 王春, 有机化学, 2009, 29, 1018.)
[2] (a) Sulzer-Mossé, S.; Alexakis, A. Chem. Commun. 2007, 3123.
(b) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
(c) Guan, X.-Y.; Yang, L.-P.; Hu, W.-H. Angew. Chem., Int. Ed. 2010, 49, 2190.
(d) Li, M.-F.; Guo, X.; Jin, W.-F.; Zheng, Q.; Liu, S.-Y.; Hu, W.-H. Chem. Commun. 2016, 52, 2736.
(e) Jia, Y.-B.; Zhang, R.; Xie, B.; Chen, G.-S.; Liu, T.-S.; Chen, Y.-X. J. Guangzhou Univ. (Nat. Sci. Ed.) 2009, 13, 47(in Chinese). (贾永兵, 张睿, 谢彬, 陈国术, 刘天穗, 陈亿新, 广州大学学报(自然科学版), 2009, 13, 47.)
[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] (a) Rueping, M.; Nachtsheim, B.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593.
(b) Yang, W.; Pan, X.-J.; Yang, D.-Q. Chin. J. Org. Chem. 2015, 35, 1216(in Chinese). (杨文, 潘雪静, 杨定乔, 有机化学, 2015, 35, 1216.)
[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] (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] (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] (a) Sigman, M. S.; Vachal, P.; Jacobsen, E. Angew. Chem., Int. Ed. 2000, 39, 1279.
(b) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
(c) Zuend, S. J.; Matthew, P. C.; Mathieu, P. L.; Jacobsen, E. N. Nature 2009, 461, 968.
(d) Zhang, C.-H.; Yang, J.; Zhou, W.-Q.; Tan, Q.-Y.; Yang, Z.; He, L.; Zhang, M. Org. Lett. 2019, 21, 8620.
(e) Zhang, Y.-P.; You, Y.; Zhao, J.-Q.; Zhang, X.-M.; Xu, X.-Y.; Yuan, W.-C. J. Org. Chem. 2019, 84, 7984.
(f) Li, X.-L.; Kong, X.-W.; Yang, S.; Meng, M.; Zhan, X.-Y.; Zeng, M.; Fang, X.-Q. Org. Lett. 2019, 21, 1979.
(g) Lu, N.; Fang, Y.-H.; Gao, Y.; Wei, Z.-L.; Cao, J.-G.; Liang, D.-P.; Lin, Y.-J.; Duan, H.-F. J. Org. Chem. 2018, 83, 793.
(h) Ma, Z.-W.; Liu, X.-F.; Liu, J.-T.; Tao, J.-C. Chin. J. Org. Chem. 2018, 38, 183(in Chinese). (马志伟, 刘晓锋, 刘俊桃, 陶京朝, 有机化学, 2018, 38, 183.)
Options
Outlines

/

〈 〉