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Title

Fragmentation of carbohydrate anomeric alkoxyl radicals: Synthesis of chiral polyhydroxylated β-iodo- and alkenylorganophosphorus(V) compounds

AuthorsHernández-Guerra, Daniel ; Rodríguez Morales, María S. ; Suárez, Ernesto
KeywordsCarbohydrates
Phosphorus
Cycli­zation
Radicals
Synthetic methods
Issue DateAug-2014
PublisherWiley-VCH
ChemPubSoc Europe
CitationEuropean Journal of Organic Chemistry 2014(23): 5033-5055 (2014)
AbstractA direct approach to β‐iodophosphonates and β‐iodophosphine oxides from 2,3‐dideoxy‐3‐phosphoryl carbohydrate derivatives has been achieved by using the anomeric alkoxyl radical 1,2‐fragmentation protocol. The reaction has been conducted on carbohydrate derivatives under mild conditions with (diacetoxyiodo)benzene and molecular iodine. Subsequent dehydroiodination afforded the corresponding vinylphosphonates and vinylphosphine oxides.
Publisher version (URL)https://doi.org/10.1002/ejoc.201402387
URIhttp://hdl.handle.net/10261/179992
Identifiersdoi: 10.1002/ejoc.201402387
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(IPNA) Artículos
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