A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

作者:Goh Kelvin Kau Kiat; Kim Sunggak*; Zard Samir Z
来源:Journal of Organic Chemistry, 2013, 78(23): 12274-12279.
DOI:10.1021/jo402169v

摘要

An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

  • 出版日期2013-12-6
  • 单位南阳理工学院