Acta Phys. -Chim. Sin. ›› 2009, Vol. 25 ›› Issue (12): 2461-2466.doi: 10.3866/PKU.WHXB20091107

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Asymmetric Hydrogenation of Benzalacetone Catalyzed by (1S,2S)-DPEN Modified 3%Ir/SiO2/2TPP Catalysts

WU Jia-Man, JIANG He-Yan, FU Hai-Yan, CHEN Hua, LI Rui-Xiang, LI Xian-Jun   

  1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
  • Received:2009-05-06 Revised:2009-07-27 Published:2009-11-27
  • Contact: CHEN Hua E-mail:scuhchen@163.com

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Abstract:

The enantioselective hydrogenation of benzalacetone catalyzed by the chiral diamine [(1S,2S)-1,2-diphenyl-1,2-ethylenediamine] ((1S,2S)-DPEN) modified 3%(w)Ir/SiO2/2TPP (TPP=triphenylphosphine) was investigated. We found that (1S,2S)-DPEN could accelerate the rate of the reaction and efficiently increase the selectivity for C=O bond hydrogenation. Under the optimumreaction conditions, a LiOH concentration of 0.375 mol·L-1 in methanol, a reaction temperature of 40 ℃, a H2 pressure of 6.0 MPa and reaction time of 8 h, the conversion of benzalacetone was more than 99.0%and the selectivity for unsaturated alcohol was more than 99.0%. The enantiomeric excess (ee) value of the unsaturated alcohol reached 48.1%.

Key words: Asymmetric hydrogenation, Supported catalyst, Chiral diamine, Benzalacetone, Iridium