Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3454-3459.DOI: 10.6023/cjoc201904081 Previous Articles     Next Articles

Special Issue: 元素有机化学合辑2018-2019 有机硅化学合辑


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;
  • 基金资助:

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).

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