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   

  1. 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 出版日期:2014-09-25 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 Yanzhaoa, Wang Jianxiaa, Liu Delonga, Zhang Wanbina,b   

  1. 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 Online:2014-09-25 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