有机化学 ›› 2019, Vol. 39 ›› Issue (12): 3454-3459.DOI: 10.6023/cjoc201904081 上一篇    下一篇

所属专题: 元素有机化学合辑2018-2019 有机硅化学合辑

研究论文

多取代烯丙基硅化合物的立体选择性合成研究

姜铨, 何玲, 李卫东   

  1. 重庆大学药学院 天然产物全合成与创新药物研究重庆市重点实验室 重庆 401331
  • 收稿日期:2019-04-30 修回日期:2019-07-25 发布日期:2019-08-30
  • 通讯作者: 何玲, 李卫东 E-mail:heling2015@cqu.edu.cn;wdli@cqu.edu.cn
  • 基金资助:
    国家自然科学基金(Nos.21672030,21702023)资助项目.

Studies on the Stereoselective Synthesis of Functionalized Allylsilane Compounds

Jiang Quan, He Ling, Li Weidong   

  1. a Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331
  • Received:2019-04-30 Revised:2019-07-25 Published:2019-08-30
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21672030, 21702023).

烯丙基硅化合物是一类重要的有机合成中间体,能参与多种类型的化学转化反应,被广泛应用于C—C键构建和复杂化合物的合成反应中,探索官能化烯丙基硅化合物的立体选择性合成对丰富有机合成方法学研究有重要意义.利用有机硅取代的环丙基三级醇化合物的Julia烯烃化反应,得到了一系列新型的烷氧甲基取代的高碘代烯丙基硅化合物.相对于烷基取代的三级醇底物,芳基取代的三级醇底物能得到立体选择性更好的产物.

关键词: 烯丙基硅, Julia烯烃化反应, 环丙基甲醇, 格氏试剂

Allylsilanes have emerged as synthetically useful intermediates that can undergo a variety of chemical transformations and have been found versatile applications in C-C bond construction as well as in preparation of complex molecules. Exploration on the stereoselective route to functionalized allylsilanes is of great significance for the development of organic synthetic methodology. An efficient pathway to a series of novel alkoxy-substituted homoiodio-allylsilanes via the Julia olefination of silylmethyl cyclopropyl carbinols was described. Carbinols derived from cyclopropyl aryl ketone were evidenced to be superiorer in controlling the stereoselectivity of the products than the alkyl equivalents.

Key words: allylsilane, Julia olefination, cyclopropyl carbinol, Grignard reagent