Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl2(BISBI)(R,R-DPEN)

Abstract

The synthesis of ruthenium complex, RuCl₂(BISBI)(R,R-DPEN) (1) [BISBI: 2,2'-bis(diphenylphosphinomethyl)-1,1'-biphenyl, DPEN: 1,2-diphenylethylenediamine] and the application to the asymmetric hydrogenation of acetophenone are reported. The effect of reaction temperature, hydrogen pressure, base concentration and molar ratio of substrate to catalyst on the activity and enantioselectivity of ruthenium catalyzed asymmetric hydrogenation of acetophenone was investigated in the iso-propanol solution of KOH. The results showed that the increase of temperature and pressure accelerated the reaction rate but just decreased slightly the enantioselectivity. Under the optimum conditions of ketone∶KOH∶Ru＝30000∶250∶1 (molar ratio), 2 MPa, 35 ℃, 6 h, the hydrogenation of acetophenone gave S-1-phenylethanol with 65% ee and 100% of yield.

Key words: acetophenone, ruthenium complex, chiral diamine, asymmetric hydrogenation

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TAO Ming^1,2,CHEN Li,XIONG Wei^1,2,YUAN Mao-Lin
CHEN Hua*^,1,LI Xian-Jun. Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl₂(BISBI)(R,R-DPEN)[J]. Chin. J. Org. Chem., 2006, 26(04): 559-562.

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RuCl₂(BISBI)[(R,R)-DPEN]催化苯乙酮不对称加氢反应研究

Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl₂(BISBI)(R,R-DPEN)

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RuCl2(BISBI)[(R,R)-DPEN]催化苯乙酮不对称加氢反应研究