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化学学报
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化学学报 ›› 2005, Vol. 63 ›› Issue (20): 1927-1930. 上一篇    下一篇

研究论文

手性二胺修饰的负载型钌催化剂催化芳香酮不对称加氢

熊伟1,2，黄艳轶1，陈华1，李贤均*,1   

  1. (1四川大学化学学院有机金属络合催化研究所 教育部绿色化学及技术重点实验室 成都 610064)
    (2西昌学院化学系 西昌 615022)
  • 投稿日期:2004-12-30 修回日期:2005-07-11 发布日期:2010-12-10
  • 通讯作者: 李贤均

Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Chiral Diamine Modified Ru/γ-Al2O3

XIONG Wei1,2, HUANG Yan-Yi1, CHEN Hua1, LI Xian-Jun*,1   

  1. (1 Key Laboratory of Green Chemistry and Technology of Ministry of Education of China, Institute of Homogeneous Catalysis, The College of Chemistry, Sichuan University, Chengdu 610064)
    (2 Department of Chemistry, Xichang College, Xichang 615022)
  • Received:2004-12-30 Revised:2005-07-11 Published:2010-12-10
  • Contact: LI Xian-Jun

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被引次数

1

研究了用手性修饰剂(1S,2S)-(－)-1,2-二苯基乙二胺修饰的负载型钌催化剂(Ru/γ-Al2O3)催化芳香酮的不对称加氢反应, 在KOH的异丙醇溶液中, 10～20 ℃, pH2＝5 MPa条件下, 芳香酮及其衍生物加氢产物的ee值达79.5%～85.0%, 2-乙酰基噻吩加氢产物的ee值可达86.2%. 此催化剂制备简单, 容易与产物分离, 重复使用4次, 对映选择性基本保持不变.

关键词: 钌, (1S,2S)-(－)-1,2-二苯基乙二胺, 芳香酮, 不对称加氢, 对映选择性

Asymmetric hydrogenation of acetophenone and its derivatives, acetylpyridine, five-membered heterocyclic ketones catalyzed by [1S,2S-(－)-1,2-diphenyl-1,2-ethylenediamine] (S,S-DPEN) modified Ru/γ-Al2O3 catalyst was investigated. Under the reaction conditions of 10～20 ℃, p＝5.0 MPa in KOH/i-PrOH solution, the ee value of aromatic alcohols produced from hydrogenation of acetophenone and its derivative could reach 79.5%～85.0%. The ee value of the hydrogenation product of 2-acetothiophene was 86.2% at 20 ℃ and p＝7 MPa. .The catalyst was stable in air and could be easily separated from the product and reused several times without remarkable change of the enantioselectivity.

Key words: ruthenium, (1S,2S)-(—)-1,2-diphenyl-1,2-ethylenediamine, aromatic ketone, asymmetric hydrogenation, enantioselectivity