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

doi:10.6023/cjoc201603005

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2175-2182.DOI: 10.6023/cjoc201603005 Previous Articles Next Articles

ARTICLE

手性氨基酸衍生物-钌配合物催化的酮不对称氢转移反应

李小娜, 王丽华, 周宏勇, 王家喜

河北工业大学化工学院绿色化工与高效节能重点实验室天津 300130

收稿日期:2016-03-04 修回日期:2016-04-09 发布日期:2016-05-06
通讯作者: 王家喜 E-mail:wangjiaxi@hebut.edu.cn
基金资助:
河北省自然科学基金（No.2011202087）资助项目.

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

Li Xiaona, Wang Lihua, Zhou Hongyong, Wang Jiaxi

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

Received:2016-03-04 Revised:2016-04-09 Published:2016-05-06
Supported by:
Project supported by the Natural Science Foundation of Hebei Province (No.2011202087).

1. Chiral Amino-acids Derivatives-Ruthenium Catalyzed Asymmetric Transfer Hydrogenation of Ketones.PDF(574KB)

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]. Chin. J. Org. Chem., 2016, 36(9): 2175-2182.

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手性氨基酸衍生物-钌配合物催化的酮不对称氢转移反应

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

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