Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems

Acta Chimica Sinica ›› 2004, Vol. 62 ›› Issue (18): 1745-1750. Previous Articles Next Articles

手性羰基铁体系催化酮的不对称氢转移氢化

陈建珊, 陈玲玲, 邢雁, 陈贵, 沈伟艺, 董振荣, 李岩云, 高景星

厦门大学化学系, 固体表面物理化学国家重点实验室, 厦门, 361005

投稿日期:2004-03-29 修回日期:2004-06-04 发布日期:2014-02-17
通讯作者: 高景星,E-mail:cuihua@jingxian.xru.edu.cn E-mail:cuihua@jingxian.xru.edu.cn
基金资助:
国家自然科学基金(No.20373056)、福建省科技厅重大科技项目(No.2002F016)和福建省厦门市科技局重大科技项目(No.3502Z20021044)资助.

Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems

CHEN Jian-Shan, CHEN Ling-Ling, XING Yan, CHEN Gui, SHEN Wei-Yi, DONG Zhen-Rong, LI Yan-Yun, GAO Jing-Xing

Department of Chemistry, State Key Laboratory for Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005

Received:2004-03-29 Revised:2004-06-04 Published:2014-02-17

Abstract

Chiral carbonyl iron systems have seldom been used in asymmetric transfer hydrogenation of aromatic ketones. In this study, new chiral iron catalytic systems were synthesized in situ from different carbonyl iron complexes with chiral diaminodiphosphine ligands, respectively. These catalytic systems have been used for the asymmetric transfer hydrogenation of various aromatic ketones under mild conditions. The results indicated that trinuclear iron complexes were the best systems for the reactions. When the [Et₃NH]⁺[HFe₃(CO)₁₁]^- as catalyst was used for asymmetric reduction of 1,1-diphenylacetone, high enantioselectivity up to 98% was achieved. Monitoring the reaction in situ by infrared spectroscopy, it could be conjectured that the carbonyl iron cluster Fe₃(CO)₁₂ kept its trinuclear skeleton unchanged during the catalytic reaction.

Key words: carbonyl iron, chiral diaminodiphosphine ligand, aromatic ketone, asymmetric transfer hydrogenation

Cite this article

CHEN Jian-Shan, CHEN Ling-Ling, XING Yan, CHEN Gui, SHEN Wei-Yi, DONG Zhen-Rong, LI Yan-Yun, GAO Jing-Xing. Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems[J]. Acta Chimica Sinica, 2004, 62(18): 1745-1750.

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手性羰基铁体系催化酮的不对称氢转移氢化

Asymmetric Transfer Hydrogenation of Ketones Catalyzed by Chiral Carbonyl Iron Systems

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