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化学学报
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化学学报 ›› 2006, Vol. 64 ›› Issue (19): 2008-2014. 上一篇    下一篇

研究论文

基于5-孟氧基-3-溴-2(5H)-呋喃酮的环丙烷合成方法研究:碳亲核试剂启动的不对称串联反应

郭金波1, 张淅芸2, 陈庆华*,1,2   

  1. (1洛阳师范学院化学系 洛阳 471022)
    (2北京师范大学化学系 北京 100875)
  • 投稿日期:2005-12-24 修回日期:2006-03-28 发布日期:2006-10-14
  • 通讯作者: 陈庆华

Study of the Synthetic Method of Cyclopropane Derivatives Based on 3-Bromo-2,5-dihydro-5-menthyloxyfuran-2-one: Asymmetric Tandem Reaction Starting by Carbon Nucleophile

GUO Jin-Bo1; ZHANG Xi-Yun2; CHEN Qing-Hua*,1,2   

  1. (1 Department of Chemistry, Luoyang Normal College, Luoyang 471022)
    (2 Department of Chemistry, Beijing Normal University, Beijing 100875)
  • Received:2005-12-24 Revised:2006-03-28 Published:2006-10-14
  • Contact: CHEN Qing-Hua

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研究碳亲核试剂(2a～2e)与手性合成砌块, 5-孟氧基-3-溴-2(5H)-呋喃酮的不对称串联反应, 分别得到不同结构的光学活性化合物3a～3d, 4, 5和6. 通过X射线晶体分析确认了它们的立体化学结构.

关键词: 不对称串联反应, 碳-碳键形成, 光学活性, 晶体结构

The structurally different chiral compounds 3a～3d, 4, 5 and 6 with newly formed stereogenic centers were obtained via the tandem asymmetric Michael addition and internal nucleophilic substitution reaction of 3-bromo-2,5-dihydro-5-menthyloxyfuran-2-one with different carbon nucleophiles. The chemical structures of these complicated compounds were determined by analytical and spectroscopic data. The proposed structures were confirmed by the X-ray crystallographic analysis of 3a (S), 5 and 6.

Key words: tandem asymmetric reaction, carbon-carbon bond formation, optical activity, crystal structure