催化学报

催化学报 ›› 2006, Vol. 27 ›› Issue (12): 1107-1110.

• 研究论文 • 上一篇    下一篇

RuCl2[P(C6H5)3]2-(R,R)-DPEN催化萘乙酮不对称加氢反应

陶明1,熊伟1,陈华2,李贤均2   

  1. 1 西昌学院生化系, 四川西昌 615022; 2 四川大学化学学院有机金属络合催化研究所, 四川成都 610064
  • 收稿日期:2006-12-25 出版日期:2006-12-25 发布日期:2006-12-25

Asymmetric Hydrogenation of Acetonaphthone Catalyzed by RuCl2［P(C6H5)3］2-(R,R)-DPEN

TAO Ming1*, XIONG Wei1, CHEN Hua2, LI Xianjun2   

  1. 1 Department of Biology and Chemistry, Xichang College, Xichang 615022, Sichuan, China; 2 Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China
  • Received:2006-12-25 Online:2006-12-25 Published:2006-12-25

PDF

873

被引次数

16

摘要： 合成了(R,R)-1,2-二苯基乙二胺((R,R)-DPEN)、 钌和三苯基膦的三元配合物RuCl2[P(C6H5)3]2-(R,R)-DPEN, 并将其用于萘乙酮的不对称加氢反应. 考察了碱/催化剂的摩尔比、反应温度和氢气压力等对催化活性和对映选择性的影响. 结果表明,多种因素对反应的转化率和对映选择性均有影响. 在萘乙酮:(CH3)3COK:催化剂摩尔比为 50000:450:1, 氢气压力为4 MPa, 反应温度为25 ℃的条件下,反应16 h时,萘乙酮生成α-萘乙醇的产率和对映选择性分别达到了100%和83%.

关键词: 钌膦配合物, 手性二胺, 萘乙酮, 不对称催化加氢, &alpha, -萘乙醇, 对映选择性

Abstract: A novel ruthenium complex RuCl2［P(C6H5)3］2-(R,R)-DPEN (DPEN=1,2-diphenylethylene-diamine) was synthesized and characterized by 1H and 31P NMR. The ruthenium complex was applied to the asymmetric hydrogenation of acetonaphthone.The effects of reaction temperature, hydrogen pressure, and molar ratio of base to catalyst on the activity and enantioselectivity were investigated in an isopropanol solution of (CH3)3COK. The results showed that the increase in the temperature and pressure accelerated the reaction but slightly decreased the enantioselectivity for (S)-α-naphthylethanol. Under the conditions of acetonaphthone∶(CH3)3COK∶Ru=50000∶450∶1 (molar ratio), 4 MPa, 25 ℃, and 16 h, 83% ee and 100% yield of α-naphthylethanol were achieved.

Key words: ruthenium phosphine complex, chiral diamine, acetonaphthone, asymmetric hydrogenation, α-naphthylethanol, enantioselectivity