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Title: | Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral β-iodo azides, vinyl azides, and 2H-azirines |
Authors: | Alonso-Cruz, Carmen R. CSIC; Kennedy, Alan R.; Rodríguez Morales, María S. CSIC ORCID ; Suárez, Ernesto CSIC ORCID | 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 | DOI: | 10.1021/ol035435g | ISSN: | 1523-7060 |
Appears in Collections: | (IPNA) Artículos |
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