Diastereoselective Synthesis of CF3-Substituted, Epoxide-Fused Heterocycles with beta-(Trifluoromethyl)vinylsulfonium Salts

Sven P. Fritz, Thomas H. West, Eoghan M. McGarrigle*, Varinder K. Aggarwal

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

51 Citations (Scopus)

Abstract

CF3-substituted vinyl diphenylsulfonium triflate is an effective annulation reagent for the formation of alpha-CF3 substituted, epoxide-fused heterocycles (pyrrolidines, piperidines, and tetrahydrofurans). This simple method affords a variety of valuable heterocyclic building blocks in a highly diastereoselective manner (dr>20:1).

Original languageEnglish
Pages (from-to)6370-6373
Number of pages4
JournalOrganic Letters
Volume14
Issue number24
DOIs
Publication statusPublished - 21 Dec 2012

Keywords

  • VINYL SULFONIUM SALTS
  • MEDICINAL CHEMISTRY
  • CONVENIENT METHOD
  • STRAIGHTFORWARD SYNTHESIS
  • ASYMMETRIC-SYNTHESIS
  • ALPHA-IMIDOSTYRENES
  • EFFICIENT SYNTHESIS
  • TANDEM REACTIONS
  • FLUORINE
  • TRIFLATE

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