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

Research output: Contribution to journalArticle

42 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.
LanguageEnglish
Pages2326-2331
Number of pages5
JournalAngewandte Chemie
Volume40
Issue number12
DOIs
Publication statusPublished - 18 Jun 2001

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Carbohydrates
Sugar Alcohols
Synthetic Chemistry Techniques
Bromine
Benzene
Carbon
alkoxyl radical

Keywords

  • carbohydrates
  • chirality
  • halides
  • iodine
  • radical reactions

Cite this

Gonzalez, C.C. ; Kennedy, A.R. ; Leon, E.I. ; Riesco-Fagundo, C. ; Suarez, E. / Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds. In: Angewandte Chemie. 2001 ; Vol. 40, No. 12. pp. 2326-2331.
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Fragmentation of carbohydrate anomeric alkoxy radicals: A new synthesis of chiral 1-halo-1-iodo compounds. / Gonzalez, C.C.; Kennedy, A.R.; Leon, E.I.; Riesco-Fagundo, C.; Suarez, E.

In: Angewandte Chemie, Vol. 40, No. 12, 18.06.2001, p. 2326-2331.

Research output: Contribution to journalArticle

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AU - Suarez, E.

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KW - carbohydrates

KW - chirality

KW - halides

KW - iodine

KW - radical reactions

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