One-pot stereoselective synthesis of anti 3-alkyl and 3-aryl-N-p-tosyl- aziridine-2-ketones and 3-aryl-N-p-tosyl-aziridine-2-carboxylates

Dianjun Chen, Cody Timmons, Li Guo, Xin Xu, Guigen Li

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

An efficient and practical synthesis of N-p-tosyl-aziridine-2-ketones and carboxylates through the use of α,β-unsaturated esters and ketones has been reported. The synthesis was conducted via a one-pot procedure consisting of aminohalogenation and in situ intramolecular SN2 substitution. Triethylamine was found to be an effective base for the in situ cyclization for most substrates. Interestingly, for several enone cases, a slightly modified procedure in which 1.0 equivalent of p-TsNCl2 was slowly added into 2.0 equivalents of enone for aminohalogenation followed by quenching with aqueous Na2SO3 resulted in crude aziridines which were proven to be nearly pure by the crude 1H NMR analysis. Moderate to good yields and excellent anti stereoselectivity were achieved for 21 examples.

Original languageEnglish
Pages (from-to)2479-2484
Number of pages6
JournalSynthesis
Issue number15
DOIs
StatePublished - Oct 18 2004

Keywords

  • Aminohalogenation
  • Aziridination
  • Cinnamates
  • Enones
  • Haloamines

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