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 (http://dx.doi.org/10.1021/ol035435g)

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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.

ORCID iDs

Alonso-Cruz, C.R., Kennedy, A.R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Rodriguez, M.S. and Suarez, E.;
  • Item type:Article
    ID code:1017
    Dates:
    Date
    Event
    4 September 2003
    Published
    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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