Synthesis of polyhydroxylated 2h-azirines and 2-halo-2h-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation

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

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.
Original languageEnglish
Pages (from-to)4116-4122
Number of pages6
JournalJournal of Organic Chemistry
Volume73
Issue number11
DOIs
Publication statusPublished - 6 Jun 2008

Keywords

  • nucleophilic-substitution reactions
  • resolution nmr-spectroscopy
  • diels-alder reactions
  • x-ray-structure
  • vinyl azides
  • convenient synthesis
  • stereospecific introduction
  • allylic substitutions
  • asymmetric-synthesis
  • dysidea-fragilis

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    Pure And Applied Chemistry

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