有机化学 ›› 1997, Vol. 17 ›› Issue (1): 76-81. 上一篇    下一篇

研究论文

手性3-氧杂双环[3.1.0]-己-2-酮类化合物的不对称合成

史海健;魏琦;吴蕙君   

  1. 安徽师范大学化学系;华东师范大学化学系
  • 发布日期:1997-02-25

Simple asymmetric synthesis of optically active 3-oxabicyclo- [3.1.0]-hex-2-one derivatives

SHI HAIJIAN;WEI QI;WU HUIJUN   

  • Published:1997-02-25

采用手性铜催化剂(S)-7644, 利用重氮醋酸不饱和酯的分子内不对称卡宾加成环化, 合成了七个光学活性3-氧杂双环[3.1.0]-己-2-酮类化合物。产品经元素分析、红外、核磁确证了结构, 并测定了比旋光度和光学收率。

关键词: 不饱和酯, 加成反应, 红外分光光度法, 双环化合物, 铜催化剂, 环化, 元素分析, 酮, 核磁共振谱法, 氮杂环化合物

Seven optically active 3-oxabicyclo-[3.1.0]-hex-2-one derivatives (or bicyclic lactones) were prepared from unsaturated esters of diazoacetic acid by the asymmetric intramolecular carbon addition under the action of a chiral copper catalyst, (S)-7644. The merit of this method is its simple operation using commercially available reagents. The structure of the products obtained were confirmed by elemental analysis, IR, NMR and the specific rotation, the e. e. values were also determined.

Key words: UNSATURATED ESTERS, ELEMENTAL ANALYSIS, ADDITION REACTION, BICYCLIC COMPOUND, CYCLIZATION, KETONE, NMR SPECTROMETRY, NITROGEN HETEROCYCLICS, INFRARED SPECTROPHOTOMETRY

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