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Título : Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral β-iodo azides, vinyl azides, and 2H-azirines
Autor : Alonso-Cruz, Carmen R., Kennedy, Alan R., Rodríguez Morales, María S., Suárez, Ernesto
Fecha de publicación : 4-Sep-2003
Editor: American Chemical Society
Resumen: 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 β-iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These β-iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.
Descripción : 4 pages, 1 table, 1 scheme.-- PMID: 14507216 [PubMed].-- Printed version published Oct 2, 2003.-- Supporting information available at:
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ISSN: 1523-7060
DOI: 10.1021/ol035435g
Citación : Organic Letters 5(20): 3729-3732 (2003)
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