Citation: WU Jia-Man, JIANG He-Yan, FU Hai-Yan, CHEN Hua, LI Rui-Xiang, LI Xian-Jun. Asymmetric Hydrogenation of Benzalacetone Catalyzed by (1S,2S)-DPEN Modified 3%Ir/SiO2/2TPP Catalysts[J]. Acta Physico-Chimica Sinica, 2009, 25(12): 2461-2466. doi: 10.3866/PKU.WHXB20091107
(1S,2S)-DPEN修饰的3%Ir/SiO2/2TPP催化苄叉丙酮的不对称加氢
在温和的条件下制备了负载型3%(w)Ir/SiO2/2TPP(三苯基膦)催化剂, 并且考察了(1S,2S)-1,2-二苯基乙二胺[(1S,2S)-DPEN]作为手性修饰剂对其催化苄叉丙酮不对称加氢反应性能的影响. 结果表明, 手性修饰剂(1S,2S)-DPEN的加入, 对苄叉丙酮不对称加氢反应活性和C=O加氢的选择性都有很好的促进作用. 经优化条件, 在40 ℃下, LiOH浓度为0.375 mol·L-1的甲醇溶液中, 氢气压力为6 MPa, 反应8 h后, 苄叉丙酮的转化率大于99.0%, 对不饱和醇的选择性大于99.0%, 不饱和醇的对映选择性(ee)值达到48.1%.
English
Asymmetric Hydrogenation of Benzalacetone Catalyzed by (1S,2S)-DPEN Modified 3%Ir/SiO2/2TPP Catalysts
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%.
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Key words:
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Asymmetric hydrogenation
- / Supported catalyst
- / Chiral diamine
- / Benzalacetone
- / Iridium
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