Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds

C.C. Gonzalez, A.R. Kennedy, E.I. Leon, C. Riesco-Fagundo, E. Suarez

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43 Citations (Scopus)

Abstract

The reaction of 1,2-halohydrins derived from easily available carbohydrates with (diacetoxyiodo)benzene (DIB) in the presence of bromine is a mild procedure for the synthesis of 1-deoxy-1-halo-1-bromo-alditols with one carbon less than the original carbohydrate. The reaction goes through β-fragmentation of the intermediate anomeric alkoxyl radicals. These 1-halo-1-bromo polyhydroxy compounds may be valuable synthetic intermediates in organic synthesis.
Original languageEnglish
Pages (from-to)2326-2331
Number of pages5
JournalAngewandte Chemie
Volume40
Issue number12
DOIs
Publication statusPublished - 18 Jun 2001

Keywords

  • carbohydrates
  • chirality
  • halides
  • iodine
  • radical reactions

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