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Fragmentation of carbohydrate anomeric alkoxy radicals: a new synthesis of chiral 1-halo-1-bromo compounds

AuthorsGonzález Martín, Concepción C. ; León, Elisa I. ; Riesco-Fagundo, Concepción ; Suárez, Ernesto
Issue Date19-Jul-2003
CitationTetrahedron Letters 44(33): 6347-6350 (2003)
AbstractThe 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.
Description4 pages, 2 tables.-- Printed version published Aug 11, 2003.
Publisher version (URL)http://dx.doi.org/10.1016/S0040-4039(03)01399-6
Appears in Collections:(IPNA) Artículos
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