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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

Alonso-Cruz, Carmen R. and Kennedy, Alan R. and Rodriguez, Maria S. and Suarez, Ernesto (2007) Alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-hexopyranoses: a new entry to chiral polyhydroxylated 2-azido-1-halo-1-alkenes. Tetrahedron Letters, 48 (40). pp. 7207-7210. ISSN 0040-4039

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Abstract

A 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. (C) 2007 Elsevier Ltd. All rights reserved.

Item type: Article
ID code: 35260
Keywords: x-ray structure, vinyl azides, olefins, facile synthesis, stereochemistry, isomerization, heterocycles, Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
    Depositing user: Pure Administrator
    Date Deposited: 02 Nov 2011 15:15
    Last modified: 17 Jul 2013 11:15
    URI: http://strathprints.strath.ac.uk/id/eprint/35260

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