Abstract
The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the D-gluco, D-galacto, D-lacto, and L-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These -iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These -iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.
Original language | English |
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Pages (from-to) | 3729-3732 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 5 |
Issue number | 20 |
DOIs | |
Publication status | Published - 4 Sept 2003 |
Keywords
- reaction of 3-azido-2
- 3-dideoxy-hexopyranose compounds
- D-gluco
- D-galacto
- D-lacto
- L-arabino
- carbohydrate
- benzene
- iodine
- dehydroiodination
- heterocyclic systems