Citation: 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 shu

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

1.
Key Laboratory of Green Chemical Technology & High Efficient Energy, School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Corresponding author: Wang Jiaxi, wangjiaxi@hebut.edu.cn
Received Date: 4 March 2016
Revised Date: 9 April 2016

Fund Project: the Natural Science Foundation of Hebei Province 2011202087

Figures(4)

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.
- asymmetric catalysis,
- enantioselectivity,
- hydrogen transfer
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沈阳化工大学材料科学与工程学院沈阳 110142