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Chinese Journal of Organic Chemistry >

2016 , Vol. 36 >Issue 9: 2175 - 2182

DOI: https://doi.org/10.6023/cjoc201603005

ARTICLE

Chiral Amino-acids Derivatives-Ruthenium Catalyzed Asymmetric Transfer Hydrogenation of Ketones

  • Li Xiaona ,
  • Wang Lihua ,
  • Zhou Hongyong ,
  • Wang Jiaxi
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  • Key Laboratory of Green Chemical Technology & High Efficient Energy, School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Received date: 2016-03-04

  Revised date: 2016-04-09

  Online published: 2016-05-06

Supported by

Project supported by the Natural Science Foundation of Hebei Province (No.2011202087).

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Abstract

Benzimidazoles derived from chiral amino acids and benzimidazoles derived from dipeptides were prepared and proved to be efficient ligands in the ruthenium catalyzed asymmetric transfer hydrogenation of acetophenone. Employing ligand 2 in the reduction of acetophenone resulted in better activity and enantioselectivity (with 15400 h-1 TOF and 77% ee). Through structure-activity correlations, the corresponding metal-ligand bifunctional mechanism was speculated. In addition, the catalytic system of[RuCl2(p-cymene)]2/2 exhibited reversed temperature effects, which explained through kinetics data. The enantioselectivity was increased from 38% to 43% when LiCl was added in dipeptides derived benzimidazoles 7/[RuCl2(p-cymene)]2 catalyzed asymmetric transfer hydrogenation.

Key words： asymmetric catalysis; enantioselectivity; hydrogen transfer

Cite this article

Li Xiaona , Wang Lihua , Zhou Hongyong , Wang Jiaxi . Chiral Amino-acids Derivatives-Ruthenium Catalyzed Asymmetric Transfer Hydrogenation of Ketones[J]. Chinese Journal of Organic Chemistry, 2016 , 36(9) : 2175 -2182 . DOI: 10.6023/cjoc201603005

References

[1] (a) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300. (b) Zhang, B.; Wang, H.; Lin, G. Q.; Xu, M. H. Eur. J. Org. Chem. 2011, 4205. (c) Kang, G.; Lin, S.; Shiwakoti, A.; Ni, B. Catal. Commun. 2014, 57, 111.
[2] (a) Wu, X. F.; Vinci, D.; Ikariya, T.; Xiao, J. L. Chem. Commun. 2005, 4447. (b) Denizalti, S.; Mercan, D.; Sen, B.; Gökçe, A. G.; Çetinkaya, B. J. Organomet. Chem. 2015, 779, 62. (c) Liu, X.; Zhang, T.; Hu, Y.; Shen, L. Catal. Lett. 2014, 144, 1289.
[3] (a) Wu, X. F.; Li, X. H.; McConville, M.; Saidi, O.; Xiao, J. L. J. Mol. Catal A:Chem. 2006, 247, 153. (b) Chakka, S. K.; Andersson, P. G.; Maguire, G. E. M.; Kruger, H. G.; Govender, T. Eur. J. Org. Chem. 2010, 972. (c) Heyan, J. J. Chem. Res. 2013, 37, 761. (d) Carmona, D.; Viguri, F.; Lamata, M. P.; Ferrer, J.; Bardají, E.; Lahoz, F. J.; GarcíaOrduña, P.; Oro, L. A. Dalton Trans. 2012, 41, 10298.
[4] (a) Sheeba, M. M.; Tamizh, M. M.; Farrugia, L. J.; Endo, A.; Karvembu, R. Organometallics 2014, 33, 540. (b) Isik, U.; Aydemir, M.; Meriç, N.; Durap, F.; Kayan, C. J. Mol. Catal. A:Chem. 2013, 379, 225. (c) Zeng, L.; Wu, F.; Li, Y. Y.; Dong, Z. R.; Gao, J. X. J. Org. Chem. 2014, 762, 34.
[5] Ye, W.; Zhao, M.; Yu, Z. Chem. Eur. J. 2012, 18, 10843.
[6] Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
[7] Manville, C. V.; Docherty, G.; Padda, R.; Wills, M. Eur. J. Org. Chem. 2011, 6893.
[8] Huynh, K. D.; Ibrahim, H.; Toffano, M.; Vo-Thanh, G. Tetrahedron:Asymmetry 2010, 21, 1542.
[9] Jerphagnon, T.; Haak, R.; Berthiol, F.; Gayet, A. J. A.; Ritleng, V.; Holuigue, A.; Pannetier, N.; Pfeffer, M.; Voelklin, A.; Lefort, L.; Verzijl, G.; Tarabiono, C.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Top. Catal. 2010, 53, 1002.
[10] Ye, W.; Zhao, M.; Du, W.; Jiang, Q.; Wu, K.; Wu, P.; Yu, Z. Chem. Eur. J. 2011, 17, 4737.
[11] (a) Lin, J.; Tian, H.; Jiang, Y.; Huang, W.; Zheng, L.; Zhang, S. Tetrahedron:Asymmetry 2011, 22, 1434. (b) He, J.; Chen, Q.; Ni, B. Tetrahedron Lett. 2014, 55, 3030.
[12] (a) Ohta, T.; Nakahara, S. I.; Shigemura, Y.; Hattori, K.; Fu-rukawa, I. Appl. Organomet. Chem. 2001, 15, 699. (b) Tinnis, F.; Adolfsson, H. Org. Biomol. Chem. 2010, 8, 4536. (c) Cambeiroa, X. C.; Pericàs, M. A. Adv. Synth. Catal. 2011, 353, 113. (d) Geoghegan, P.; O'Leary, P. Tetrahedron:Asymmetry 2010, 21, 867. (e) Ahlford, K.; Ekström, J.; Zaitsev, A. B.; Ryberg, P.; Eriksson, L.; Adolfsson, H. Chem. Eur. J. 2009, 15, 11197. (f) Li, X. N.; Zhou, H. Y.; Feng, L.; Duan, K.; Wang, J. X. Chin. J. Org. Chem. 2012, 32, 19(in Chinese).
[13] Li, X. N.; Zhang, P. L.; Duan, K.; Wang, J. X. Appl. Organomet. Chem. 2012, 26, 168.
[14] Vastila, P.; Zaitser, A. B.; Wettergren, J.; Privalov, T.; Adolfsson, H. Chem. Eur. J. 2006, 12, 3218.
[15] (a) Sandoval, C. A.; Ohkuma, T.; Utsumi, N.; Tsutsumi, K.; Murata, K.; Noyori, R. Chem. Asian. J. 2006, 1~2, 102. (b) Sandoval, C. A.; Ding, Y.; Li, K.; Noyori, R. Chem. Asian J. 2008, 3, 1801.

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