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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (07): 1250-1253. 上一篇    下一篇

研究简报

含松香骨架的手性氮杂冠醚的合成及其在不对称Michael 加成反应中的应用

杨 林 ; 唐莅东; 潘英明 ; 王恒山* ; 苏桂发* ; 梁 敏   

  1. (广西师范大学化学化工学院 桂林 541004)
  • 收稿日期:2007-07-11 修回日期:2007-11-29 发布日期:2008-07-28
  • 通讯作者: 王恒山* ; 苏桂发

Synthesis and Catalytic Activities of Chiral Azacrown Ethers Derived from Rosin

YANG, Lin ; TANG, Li-Dong ; PAN, Ying-Ming ; WANG, Heng-Shan*
SU, Gui-Fa* ; LIANG, Min
  

  1. (School of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004)
  • Received:2007-07-11 Revised:2007-11-29 Published:2008-07-28
  • Contact: WANG, Heng-Shan*

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1253

被引次数

12 | 3

以松香为原料, 合成了4个手性氮杂冠醚: N-脱氢松香基单氮杂-12-冠-4、N-脱氢松香基单氮杂-15-冠-5、N-脱氢松香基单氮杂-18-冠-6和N-降解脱氢松香基单氮杂-12-冠-4, 并用于催化不对称查尔酮Michael加成反应, 发现这些手性氮杂冠醚可以有效地催化2-硝基丙烷与查尔酮的不对称Michael加成, Michael加成产物ee最高达35%.

关键词: 松香, 不对称Michael加成, 合成, 手性氮杂冠醚, 查尔酮

Four chiral azacrown ethers were synthesized from rosin: N-dehyroabietyl monoaza-12-crown-4, N-dehyroabietyl monoaza-15-crown-5, N-dehyroabietyl monoaza-18-crown-6 and N-degrading-
dehyroabietyl monoaza-12-crown-4, which were employed as phase-transfer catalysts in asymmetric Mi-chael addition of 2-nitropropane to chalcone, affording the corresponding Michael addition products up to
35% ee.

Key words: synthesis, rosin, chiral azacrown ether, asymmetric Michael addition, chalcone