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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1724-1728. 上一篇    下一篇

研究论文

新型联吡啶双膦配体的合成及其在β-酮酸酯不对称加氢反应中的应用

陈 丽a ; 马梦林b; 彭宗海a; 陈 华*,a   

  1. (a四川大学化学学院有机金属络合催化研究所 绿色化学与技术教育部重点实验室 成都 610064)
    (b西华大学化学系 成都 611930)
  • 收稿日期:2007-07-13 修回日期:2008-03-20 发布日期:2008-10-20
  • 通讯作者: 陈 华

Synthesis of a New Bipyridyl Diphosphine Ligand and Its Application to Asymmetric Hydrogenation of β-Keto Esters

CHEN, Lia ; MA, Meng-Linb ; PENG, Zong-Haia ; CHEN, Hua*,a   

  1. (a Key Laboratory of Green Chemistry & Technology, Ministry of Education, Institute of Homogeneous Catalysis,
    Faculty of Chemistry, Sichuan University, Chengdu 610064)
    (b Department of Chemistry, Xihua University Chengdu 611930)
  • Received:2007-07-13 Revised:2008-03-20 Published:2008-10-20
  • Contact: CHEN, Hua

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合成了新型联吡啶手性双膦配体 (R)-MeO-P-Phos [(R)-2,2’,6,6’-四甲氧基-4,4’-二(二(对甲氧基)苯基膦基)-3,3’-联吡啶)], 并将其用于β-酮酸酯不对称加氢反应. 考察了不同溶剂对反应的影响, 在乙醇中对乙酰乙酸乙酯加氢可获得 99.1%的对映选择性; 新配体对含不同取代基的β-酮酸酯同样表现出非常高的活性和对映选择性.

关键词: 不对称加氢, β-酮酸酯, 对映选择性, 手性双膦配体

A new electron-donating diphosphine (R)-MeO-P-Phos [(R)-2,2’,6,6’-tetramethoxy-4,4’- bis[di(4-meth- oxylphenyl)phosphino]-3,3’-bipyridine] has been synthesized and its application to the asymmetric hydrogenation of β-keto esters catalyzed by ruthenium complex was explored. Solvent effect was tested and up to 99.1% ee was achieved for the hydrogenation of ethyl acetoacetate in EtOH. The asymmetric hydrogenation of various β-keto esters catalyzed by Ru-MeO-P-Phos was investigated.

Key words: β-keto ester, asymmetric hydrogenation, chiral diphosphine, enantioselectivity