化学学报 ›› 1999, Vol. 57 ›› Issue (6): 641-643. 上一篇    

研究论文

手性螺-环丙烷双内酯化合物的合成与结构

黄慧;陈庆华   

  1. 北京师范大学化学系.北京(100875)
  • 发布日期:1999-06-15

Synthesis and structure of the chiral spiro-cyclopropane derivatives

Huang Hui;Chen Qinghua   

  1. Beijing Normal Univ., Dept of Chem..Beijing(100875)
  • Published:1999-06-15

本文进一步研究了5-(l-孟氧基)-3-溴-2(5H)-呋喃酮(1)与氧的亲核试剂,如二苯甲醇、苯甲醇、α-甲基苯甲醇、薄荷醇、冰片醇发生新颖的串联不对称双Michael加成/分子内亲核取代反应,合成了一般方法难以合成的含有多个手性中心的螺[1-溴-4-l-孟氧基-5-氧杂-6-氧代双环[3.1.0]己烷-2,3'-(4'-亲核基-5'-孟氧基丁内酯)](4a-4e)。通过元素分析,IR,UV,^1HNMR,^1^3CNMR,MS,[α]~D^2^0波谱分析数据以及X四圆衍射确定了4a-4e的化学结构和绝对构型。

关键词: 环丙烷P, 内酯, 螺环化合物, 晶体结构, 迈克尔加成反应, 亲核反应, 取代反应

Tandem asymmetric reactions of 1 with nucleophilic alcohols afforded optically pure spirocyclopropane derivatives with four stereogenic centers 4a-4e in 64%-88% yields with d.e.≥98%. The optically pure compounds 4a-4e were identified on the basis of their analytical data, such as [α]~D^2^0, UV, IR, ^1H NMR, ^1^3C NMR, MS and elemental analysis. The absolute configuration of the chiral spirocyclopropane compound (4a) was established by X-ray crystallography.

Key words: CYCLOPROPANE P, LACTONES, SPIRO COMPOUNDS, CRYSTAL STRUCTURE, MICHAEL ADDITION REACTION, NUCLEOPHILIC REACTION, SUBSTITUTION REACTION

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