Synthesis of Chiral γ-Amino Alcohols via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of β-Imide Ketones

doi:10.6023/cjoc201404035

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (9): 1766-1772.DOI: 10.6023/cjoc201404035 Previous Articles Next Articles

RuPHOX-Ru催化的手性γ-氨基醇的不对称氢化合成(封面文章)

王彦兆^a, 王建霞^a, 刘德龙^a, 张万斌^a,b

a 上海交通大学药学院, 上海 200240;
b 上海交通大学化学化工学院, 上海 200240

收稿日期:2014-04-18 修回日期:2014-05-15 发布日期:2014-05-23
通讯作者: 刘德龙, 张万斌 E-mail:wanbin@sjtu.edu.cn
基金资助:
国家自然科学基金(Nos. 21172143, 21172145, 21372152, 21232004)资助项目.

Synthesis of Chiral γ-Amino Alcohols via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of β-Imide Ketones

Wang Yanzhao^a, Wang Jianxia^a, Liu Delong^a, Zhang Wanbin^a,b

a School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240;
b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2014-04-18 Revised:2014-05-15 Published:2014-05-23
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172143, 21172145, 21372152, 21232004).

The RuPHOX-Ru catalyzed asymmetric hydrogenation of β-imide ketones to afford chiral γ-primary amino alcoholsis is reported. Under the optimal reaction conditions (using Na₂CO₃ as a base, EtOH as a solvent), a series of β-imide ketones were hydrogenated in the presence of RuPHOX-Ru and H2 (5.0 MPa) to give the desired products with excellent yields and enantioselectivities (quantitative conversions and up to 98% ee). The hydrogenated products were characterized by NMR and HRMS, and their absolute configuration was also confirmed. The current procedure provides a concise and efficient synthesis of chiral γ-primary amino alcohols.

Key words: RuPHOX-Ru, chiral γ-amino alcohol, asymmetric hydrogenation, synthesis

Cite this article

Wang Yanzhao, Wang Jianxia, Liu Delong, Zhang Wanbin. Synthesis of Chiral γ-Amino Alcohols via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of β-Imide Ketones[J]. Chin. J. Org. Chem., 2014, 34(9): 1766-1772.

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RuPHOX-Ru催化的手性γ-氨基醇的不对称氢化合成(封面文章)

Synthesis of Chiral γ-Amino Alcohols via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of β-Imide Ketones

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