Chinese Journal of Catalysis

Chinese Journal of Catalysis ›› 2007, Vol. 28 ›› Issue (12): 1057-1061.

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Asymmetric Hydrogenation of Benzalacetone Catalyzed by Chiral Diamine-Modified Ru-TPP/γ-Al2O3

MING Fangyong, WANG Jinbo, FU Haiyan, CHEN Jun, CHEN Hua*, LI Xianjun   

  1. Institute of Homogeneous Catalysis, Key Lab oratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China
  • Received:2007-12-25 Online:2007-12-25 Published:2007-12-25

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Abstract: The enantioselective hydrogenation of benzalacetone was catalyzed by chiral diamine-modified Ru-TPP/γ-Al2O3(TPP=triphenylphosphine), and the effect of chiral diamines, such as (1S,2S)-DPEN ((1S,2S)-1,2-diphenyl-1,2-ethylenediamine), (S)-1,1-di(4-anisyl)-2-isopropyl-1,2-ethylenediamine, (8S,9S)-9-amino (9-deoxy) dihydrocinchonidine, and (1S,2S)-1,2-diaminocyclohexane on the hydrogenation was investigated. The results showed that (1S,2S)-DPEN could efficiently improve the hydrogenation activity and the selectivity for benzalacetone. Under the optimum reaction conditions of 40 ℃, H2 pressure of 4.0 MPa in K2CO3/i-PrOH+H2O solution, and (1S,2S)-DPEN as the chiral modifier, the conversion and the selectivity for the unsaturated alcohol reached 99% and 98%, respectively, and the ee value of the unsaturated alcohol was up to 47%.

Key words: benzalacetone, supported ruthenium catalyst, chiral diamine, asymmetric hydrogenation, unsaturated alcohol