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

AuthorsAlonso-Cruz, Carmen R. ; Kennedy, Alan R.; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date4-Sep-2003
PublisherAmerican Chemical Society
CitationOrganic Letters 5(20): 3729-3732 (2003)
AbstractThe 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.
Description4 pages, 1 table, 1 scheme.-- PMID: 14507216 [PubMed].-- Printed version published Oct 2, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol035435g
Publisher version (URL)http://dx.doi.org/10.1021/ol035435g
Appears in Collections:(IPNA) Artículos
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