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 0040-4039Full text not available in this repository. (Request a copy from the Strathclyde author)
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.
|Keywords:||x-ray structure, vinyl azides, olefins, facile synthesis, stereochemistry, isomerization, heterocycles, Chemistry, Biochemistry, Organic Chemistry, Drug Discovery|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry|
|Depositing user:||Pure Administrator|
|Date Deposited:||02 Nov 2011 15:15|
|Last modified:||23 Sep 2016 02:31|