NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups

Jon C. Loren, Antoni Krasiński, Valery V. Fokin, K. Barry Sharpless

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Abstract

NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbarnate. These organic azides were easily prepared on 0.1-mol scale in one or two steps from inexpensive commercially available materials. The cleaving properties of N-substituents in the resulting 1,2,3-triazole products with aqueous sodium hydroxide vary from

Original languageEnglish
Article numberY06505ST
Pages (from-to)2847-2850
Number of pages4
JournalSynlett
Issue number18
DOIs
Publication statusPublished - 3 Nov 2005
Externally publishedYes

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Keywords

  • Alkynes
  • Azides
  • Click chemistry
  • Cycloaddition
  • Heterocycles
  • Protecting groups
  • Triazoles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Loren, J. C., Krasiński, A., Fokin, V. V., & Sharpless, K. B. (2005). NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups. Synlett, (18), 2847-2850. [Y06505ST]. https://doi.org/10.1055/s-2005-918944