(2-Bromoethyl)sulfonium Trifluoromethanesulfonates in Stereoselective Annulation Reactions for the Formation of Fused Bicyclic Epoxides and Aziridines

Sven P. Fritz, Zulfiquar Ali, Matthew G. Unthank, Eoghan M. McGarrigle, Varinder K. Aggarwal*

*Corresponding author for this work

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

12 Citations (Scopus)

Abstract

A versatile and simple method is reported for the synthesis of bicyclic epoxide and aziridine?fused heterocycles (up to 98% yield, up to 96?:?4 er or up to 15?:?1 dr), using a tandem Michael addition/Johnson?Corey?Chaykovsky annulation approach. A new chiral (2-bromoethyl)sulfonium reagent is described, based on an easily available chiral sulfide; it promotes or enhances stereoselectivity in the reaction.

Original languageEnglish
Pages (from-to)2384-2398
Number of pages15
JournalHelvetica Chimica Acta
Volume95
Issue number12
DOIs
Publication statusPublished - Dec 2012

Keywords

  • Ylides
  • Johnson?Corey?Chaykovsky annulations
  • Cyclization reactions
  • Sulfides
  • Stereoselective synthesis
  • VINYL SULFONIUM SALTS
  • CONVENIENT METHOD
  • ENANTIOSELECTIVE SYNTHESIS
  • ASYMMETRIC EPOXIDATION
  • ALPHA-IMIDOSTYRENES
  • EFFICIENT SYNTHESIS
  • TANDEM REACTIONS
  • AMINO-ALCOHOLS
  • AMPHOTERICIN-B
  • DERIVATIVES

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