Synthesis of 1,2-dioxolanes by annulation reactions of peroxycarbenium ions with alkenes

Org Lett. 2005 Oct 13;7(21):4617-20. doi: 10.1021/ol051703u.

Abstract

[reaction: see text] The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized in three steps from the corresponding ketone and alkene.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Dioxolanes / chemical synthesis*
  • Dioxolanes / chemistry
  • Molecular Structure
  • Organosilicon Compounds / chemistry*
  • Peroxides / chemistry*
  • Trimethylsilyl Compounds / chemistry

Substances

  • Alkenes
  • Dioxolanes
  • Organosilicon Compounds
  • Peroxides
  • Trimethylsilyl Compounds
  • allyltrimethylsilane