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Alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-hexopyranoses: a new entry to chiral polyhydroxylated 2-azido-1-halo-1-alkenes

AuthorsAlonso-Cruz, Carmen R. ; Kennedy, Alan R.; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date2-Aug-2007
CitationTetrahedron Letters 48(40): 7207-7210 (2007)
AbstractA new general two-step methodology for the synthesis of chiral fluoro, chloro, bromo and iodo vinyl azides from carbohydrate-derived halohydrins has been developed. The anomeric alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-pyranoses under oxidative conditions with (diacetoxyiodo)benzene and iodine gave 2-azido-1,2-dideoxy-1-halo-1-iodo-alditols, which by chemoselective dehydroiodination afforded (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good overall yields. Preliminary thermolysis and photochemical studies of these compounds for the synthesis of hitherto unknown disubstituted 2-halo-3-alkyl-2H-azirines have also been accomplished.
Description4 pages, 2 tables, 1 scheme.-- Printed version published Oct 1, 2007.
Supporting information (experimental procedures and analytical data for all new compounds) available at: http://dx.doi.org/10.1016/j.tetlet.2007.07.190
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2007.07.190
Appears in Collections:(IPNA) Artículos
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