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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 4: 997 - 1002

DOI: https://doi.org/10.6023/cjoc201910032

Indan-f-amphox: An Efficient PNN Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of β-Aryl β-Ketoesters

  • Gu Guoxian ,
  • Hu Yang ,
  • Liu Shaodong ,
  • Dong Xiu-Qin ,
  • Zhang Xumu
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  • a School of Chemical Engineering and Technology, Tianjin Key Laboratory of Chemical Process Safety, Hebei University of Technology, Tianjin 300130, China;
    b College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072, China;
    c Department of Chemistry, Rutgers, The State University of New Jersey, Piscataway, NJ, 08854, USA;
    d Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055, China

Received date: 2019-10-28

  Revised date: 2019-11-28

  Online published: 2020-05-06

Supported by

Project supported by the Shenzhen Free Exploration Fund (No. JCYJ20170817104853520).

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Abstract

A new chiral tridentate PNN ligand, indan-f-amphox (a sister ligand of f-amphox), was synthesized and applied in iridium-catalyzed asymmetric hydrogenation of β-aryl β-ketoesters. A wide range of β-aryl β-ketoesters are reduced using an Ir(III)-indan-f-amphox catalyst with excellent enantioselectivities and reactivities (up to 99% ee, TON=10000).

Key words： PNN ligand; asymmetric hydrogenation; β-ketoesters; f-amphox

Cite this article

Gu Guoxian , Hu Yang , Liu Shaodong , Dong Xiu-Qin , Zhang Xumu . Indan-f-amphox: An Efficient PNN Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of β-Aryl β-Ketoesters[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 997 -1002 . DOI: 10.6023/cjoc201910032

References

[1] Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, Ed.:Ojima, I., Wiley-VCH, New York, 2000, p. 13.
[2] (a) Noyori R.; Kitamura M. In Modern Synthetic Methods, Ed.:Scheffold, R., Springer, Berlin, 1989, Vol. 5, p. 115.
(b) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis, Ed.:Ojima, I., VCH, New York, 1993, p. 1.
(c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
[3] (a) Chen, S.; Yang, W.; Yao, Y.; Yang, X.; Deng, Y.; Yang, D. Chin. J. Org. Chem. 2018, 38, 2534(in Chinese). (陈姝琪, 杨文, 姚永祺, 杨新, 邓颖颍, 杨定乔, 有机化学, 2018, 38, 2534.)
(b) Shan, H.; Ling, L.; Hu, J.; Zhang, H. Chin. J. Org. Chem. 2019, 39, 1548(in Chinese). (单贺, 伶俐, 胡剑锋, 张浩, 有机化学, 2019, 39, 1548.)
(c) Yuan, Q.; Zhang, W. Chin. J. Org. Chem. 2016, 36, 274(in Chinese). (袁乾家, 张万斌, 有机化学, 2016, 36, 274.)
[4] For M-NH catalysis see review:(a) Zhao, B.; Han, Z.; Ding, K. Angew. Chem., Int. Ed. 2013, 52, 4744. The recent advances in M-NH ligands see:(b) Li, Y.; Yu, S.; Wu, X.; Xiao, J.; Shen, W.; Dong, Z., Gao, J. J. Am. Chem. Soc. 2014, 136, 4031.
(c) Bao, D.-H.; Wu, H.-L.; Liu, C.-L.; Xie, J.-H.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2015, 54, 8791.
[5] Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.
[6] (a) Hashigushi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
(b) Gao, J.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087.
(c) Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron:Asymmetry 1995, 6, 705.
[7] Xie, J.-H.; Liu, X.-Y.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 7329.
[8] Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817.
[9] Li, W.; Hou, G.; Wang, C.; Jiang, Y.; Zhang, X. Chem. Commun. 2010, 46, 3979.
[10] (a) Wu, W.; Liu, S.; Duan, M.; Tan, X.; Chen, C.; Xie, Y.; Lan, Y.; Dong, X.-Q.; Zhang, X. Org. Lett. 2016, 18, 2938.
(b) Wu, W.; You, C.; Yin, C.; Liu, Y.; Dong, X.-Q.; Zhang, X. Org. Chem. Front. 2017, 4, 1499.
(c) Wu, W.; You, C.; Yin, C.; Liu, Y.; Dong, X.-Q.; Zhang, X. Org. Lett. 2017, 19, 2548.
(d) Wu, W.; Xie, Y.; Li, P.; Li, X.; Liu, Y.; Dong, X.-Q.; Zhang, X. Org. Chem. Front. 2017, 4, 555.
(e) Gu, G.; Yang, T.; Yu, O.; Qian, H.; Wang, J.; Dang, L.; Zhang, X. Org. Lett. 2017, 19, 5920.
[11] Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
[12] Xie, J.-H.; Liu, X.-Y.; Yang, X.-H.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2012, 51, 201.
[13] Hayashi, T.; Mise, T.; Fukushima, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K. Bull. Chem. Soc. Jpn. 1980, 53, 1138.
[14] Nie, H.; Zhou, G.; Wang, Q.; Chen, W.; Zhang, S. Tetrahedron:Asymmetry 2013, 24, 1567.
[15] Gu, G.; Yang, T.; Lu, J.; Wen, J.; Dang, L.; Zhang, X. Org. Chem. Front. 2018, 5, 1209.
[16] Jiang, W.; Zhao, Q.; Tan, W. Chin. J. Chem. 2018, 36, 153.
[17] (a) Schenck, T. G.; Downes, J. M.; C. Milne, R. C.; Mackenzie, P. B.; Boucher, H.; Whelan, J.; Bosnich, B. Inorg. Chem. 1985, 24, 2334.
(b) Pohl, M.; Lyon, D. K.; Mizuno, N.; Nomiya, K.; Finke, R. G. Inorg. Chem. 1995, 34, 1413.
[18] Ye, M.-C.; Li, B.; Zhou, J.; Sun, X.-L.; Tang, Y. J. Org. Chem. 2005, 70, 6108.
[19] Jiang, W.; Zhao, Q.; Tang, W. Chin. J. Chem. 2018, 36, 153.
[20] Zhang, Y.; Yu, D.; Huang, Z.; Xu, J.; Wu, X.; Wang, Y.; Wang, M.; Yang, S.; Webster, R. D.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 2416.
[21] White, N. A.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 14674.
[22] Chen, X.-S.; Hou, C.-J.; Qin, C.; Liu, H.; Liu, Y.-J.; Huang, D.-Z.; Hu, X.-P. RSC Adv. 2017, 7, 12871.
[23] Ohtani, I. I.; Hotta, K.; Ichikawa, Y.; Isobe, M. Chem. Lett. 1995, 7, 513.
[24] Andrea, K.; Michel, S.; Barbare, M. Org. Lett. 2013, 15, 1614.
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