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

Authors:Alonso-Cruz, Carmen R.
Kennedy, Alan R.
Rodríguez Morales, María S.
Suárez, Ernesto
Issue Date:4-Sep-2003
Publisher:American Chemical Society
Citation:Organic Letters 5(20): 3729-3732 (2003)
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 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.
Description:4 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
URI:http://hdl.handle.net/10261/16765
ISSN:1523-7060
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Appears in Collections:(IPNA) Artículos

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