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

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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 (https://doi.org/10.1016/j.tetlet.2007.07.190)

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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.

ORCID iDs

Alonso-Cruz, Carmen R., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Rodriguez, Maria S. and Suarez, Ernesto;
CORE (COnnecting REpositories)