The cinnamate-based aminohalogenation provides an easy access to antimethyl 3-aryl-N-p-tosyl- and N-o-nosyl-aziridine-2-carboxylates

Dianjun Chen, Sun Hee Kim, Brian Hodges, Guigen Li

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

The first application of trans-alkyl cinnamate-based aminohalogenation to the synthesis of anti methyl 3-aryl-N-(p-toluene)sulfonylaziridine-2- carboxylates and anti methyl 3-aryl-N-(o-nitrobenzene)sulfonylaziridine-2- carboxylates was described. The synthesis was easily carried out by mixing alkyl cinnamate-derived haloamines with potassium carbonate in acetonitrile at room temperature. Good to excellent yields (83-97% for N-p-Ts and 75-94% for N-o-Ns trans-aziridine-2-carboxylates, respectively) have been achieved for 11 examples.

Original languageEnglish
Pages (from-to)56-62
Number of pages7
JournalArkivoc
Volume2003
Issue number12
StatePublished - 2003

Keywords

  • Aminohalogenation
  • Aziridine
  • Cinnamate
  • Haloamine

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