Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines

C.R. Alonso-Cruz, A.R. Kennedy, M.S. Rodriguez, E. Suarez

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the D-gluco, D-galacto, D-lacto, and L-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These -iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These -iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.
Original languageEnglish
Pages (from-to)3729-3732
Number of pages3
JournalOrganic Letters
Volume5
Issue number20
DOIs
Publication statusPublished - 4 Sep 2003

    Fingerprint

Keywords

  • reaction of 3-azido-2
  • 3-dideoxy-hexopyranose compounds
  • D-gluco
  • D-galacto
  • D-lacto
  • L-arabino
  • carbohydrate
  • benzene
  • iodine
  • dehydroiodination
  • heterocyclic systems

Cite this