Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines
Alonso-Cruz, C.R. and Kennedy, A.R. and Rodriguez, M.S. and Suarez, E. (2003) Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral ß-iodo azides, vinyl azides and 2H-azirines. Organic Letters, 5 (20). pp. 3729-3732. ISSN 1523-7060
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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.
Creators(s): |
Alonso-Cruz, C.R., Kennedy, A.R. ![]() | Item type: | Article |
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ID code: | 1017 |
Keywords: | reaction of 3-azido-2, 3-dideoxy-hexopyranose compounds, D-gluco, D-galacto, D-lacto, L-arabino, carbohydrate, benzene, iodine, dehydroiodination, heterocyclic systems, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry |
Subjects: | Science > Chemistry |
Department: | Faculty of Science > Pure and Applied Chemistry |
Depositing user: | Catriona Mccallum |
Date deposited: | 15 May 2006 |
Last modified: | 26 Feb 2021 03:49 |
Related URLs: | |
URI: | https://strathprints.strath.ac.uk/id/eprint/1017 |
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