Abstract
The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These beta-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.
Original language | English |
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Pages (from-to) | 4116-4122 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 73 |
Issue number | 11 |
DOIs | |
Publication status | Published - 6 Jun 2008 |
Keywords
- nucleophilic-substitution reactions
- resolution nmr-spectroscopy
- diels-alder reactions
- x-ray-structure
- vinyl azides
- convenient synthesis
- stereospecific introduction
- allylic substitutions
- asymmetric-synthesis
- dysidea-fragilis