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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (02): 235-239. 上一篇    下一篇

研究论文

L-脯氨酸催化α-酮酰胺与甲基酮的不对称直接Aldol反应

王亚军， 沈宗旋， 丁娟，张雅文*   

  1. (苏州大学化学化工学院 江苏省有机合成重点实验室 苏州 215006)
  • 收稿日期:2006-05-08 修回日期:2006-07-10 发布日期:2007-01-30
  • 通讯作者: 张雅文

Asymmetric Aldol Reaction between Methyl Ketones and α-Ketoamides Catalyzed by L-Proline

WANG Ya-Jun, SHEN Zong-Xuan, DING Juan, ZHANG Ya-Wen*   

  1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering,
    Suzhou University, Suzhou 215006)
  • Received:2006-05-08 Revised:2006-07-10 Published:2007-01-30
  • Contact: ZHANG Ya-Wen

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用L-脯氨酸催化α-酮酰胺与甲基酮的不对称直接Aldol反应, 获得了不同光学活性的α-羟基酰胺, 产率在21%～99%之间, 对映选择性最高达到43% ee. 加成产物的结构用元素分析、红外光谱和核磁共振进行了表征.

关键词: α-酮酰胺, α-羟基酰胺, 脯氨酸, Aldol反应

Direct asymmetric aldol addition of methyl ketones to α-ketoamides was achieved using L-proline as a chiral catalyst. Various optically active α-hydroxyamides were obtained in variable yields (21%～99%) with enantioselectivity up to 43% ee. The structures of the adducts were confirmed by elemental analysis, IR, 1H NMR and 13C NMR spectra.

Key words: α-ketoamide, α-hydroxyamide, aldol addition, proline