Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 3729-3732 |
| Number of pages | 3 |
| Journal | Organic Letters |
| Volume | 5 |
| Issue number | 20 |
| DOIs | |
| Publication status | Published - 4 Sep 2003 |
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Keywords
- reaction of 3-azido-2
- 3-dideoxy-hexopyranose compounds
- D-gluco
- D-galacto
- D-lacto
- L-arabino
- carbohydrate
- benzene
- iodine
- dehydroiodination
- heterocyclic systems
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Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines. / Alonso-Cruz, C.R.; Kennedy, A.R.; Rodriguez, M.S.; Suarez, E.
In: Organic Letters, Vol. 5, No. 20, 04.09.2003, p. 3729-3732.Research output: Contribution to journal › Article
TY - JOUR
T1 - Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines
AU - Alonso-Cruz, C.R.
AU - Kennedy, A.R.
AU - Rodriguez, M.S.
AU - Suarez, E.
PY - 2003/9/4
Y1 - 2003/9/4
N2 - 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.
AB - 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.
KW - reaction of 3-azido-2
KW - 3-dideoxy-hexopyranose compounds
KW - D-gluco
KW - D-galacto
KW - D-lacto
KW - L-arabino
KW - carbohydrate
KW - benzene
KW - iodine
KW - dehydroiodination
KW - heterocyclic systems
UR - http://pubs.acs.org/cgi-bin/article.cgi/orlef7/2003/5/i20/html/ol035435g.html
UR - http://dx.doi.org/10.1021/ol035435g
U2 - 10.1021/ol035435g
DO - 10.1021/ol035435g
M3 - Article
VL - 5
SP - 3729
EP - 3732
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 20
ER -