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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Official URL: http://dx.doi.org/10.1021/ol035435g

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.

Creators(s):	Alonso-Cruz, C.R., Kennedy, A.R. ORCID: https://orcid.org/0000-0003-3652-6015, Rodriguez, M.S. and Suarez, E.;
Item type:	Article
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:	http://pubs.acs.org/cgi-bin/article.cgi/...
URI:	https://strathprints.strath.ac.uk/id/eprint/1017
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