English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/12688
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:
Title

Alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-hexopyranoses: a new entry to chiral polyhydroxylated 2-azido-1-halo-1-alkenes

AuthorsAlonso-Cruz, Carmen R. ; Kennedy, Alan R.; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date2-Aug-2007
PublisherElsevier
CitationTetrahedron Letters 48(40): 7207-7210 (2007)
AbstractA new general two-step methodology for the synthesis of chiral fluoro, chloro, bromo and iodo vinyl azides from carbohydrate-derived halohydrins has been developed. The anomeric alkoxyl radical fragmentation of 3-azido-2,3-dideoxy-2-halo-pyranoses under oxidative conditions with (diacetoxyiodo)benzene and iodine gave 2-azido-1,2-dideoxy-1-halo-1-iodo-alditols, which by chemoselective dehydroiodination afforded (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good overall yields. Preliminary thermolysis and photochemical studies of these compounds for the synthesis of hitherto unknown disubstituted 2-halo-3-alkyl-2H-azirines have also been accomplished.
Description4 pages, 2 tables, 1 scheme.-- Printed version published Oct 1, 2007.
Supporting information (experimental procedures and analytical data for all new compounds) available at: http://dx.doi.org/10.1016/j.tetlet.2007.07.190
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2007.07.190
URIhttp://hdl.handle.net/10261/12688
DOI10.1016/j.tetlet.2007.07.190
ISSN0040-4039
Appears in Collections:(IPNA) Artículos
Files in This Item:
There are no files associated with this item.
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.