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Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines

Alonso-Cruz, C.R. and Kennedy, A.R. and Rodriguez, M.S. and Suarez, E. (2003) Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines. Organic Letters, 5 (20). pp. 3729-3732. ISSN 1523-7060

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Abstract

The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the D-gluco, D-galacto, D-lacto, and L-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These -iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These -iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.