Alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-hexopyranoses: a new entry to chiral polyhydroxylated 2-azido-1-halo-1-alkenes

Carmen R. Alonso-Cruz, Alan R. Kennedy, Maria S. Rodriguez, Ernesto Suarez

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A new general two-step methodology for the synthesis of chiral fluoro, chloro, bromo and iodo vinyl azides from carbohydrate-derived halohydrins has been developed. The anomeric alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-pyranoses under oxidative conditions with (diacetoxyiodo) benzene and iodine gave 2-azido-1,2-dideoxy-1-halo-1-iodo-alditols, which by chemoselective dehydroiodination afforded (Z, E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good overall yields. Preliminary thermolysis and photochemical studies of these compounds for the synthesis of hitherto unknown disubstituted 2-halo-3-alkyl-2H-azirines have also been accomplished. (C) 2007 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)7207-7210
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number40
DOIs
Publication statusPublished - 1 Oct 2007

Keywords

  • x-ray structure
  • vinyl azides
  • olefins
  • facile synthesis
  • stereochemistry
  • isomerization
  • heterocycles

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