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Title

Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems

AuthorsMartín, Ángeles ; Pérez-Martín, Inés ; Suárez, Ernesto
KeywordsIntramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
benzene
N-Phosphoramidate
N-Cyanamide
Issue Date1-Aug-2009
PublisherElsevier
CitationTetrahedron 65(31): 6147-6155 (2009)
AbstractThe nitrogen-centred radical generated by reaction of an N-phosphoramidate or N-cyanamide, attached to a tri- or tetramethylene tether extended from the C-1 of a carbohydrate, with (diacetoxyiodo)benzene (DIB) and iodine can undergo a regio- and stereoselective intramolecular hydrogen atom transfer (HAT) reaction to furnish four different oxa-azaspirobicyclic systems: 1-oxa-6-azaspiro[4.4]nonane, 1-oxa-6-azaspiro[4.5]decane, 6-oxa-1-azaspiro[4.5]decane and 1-oxa-7-azaspiro[5.5]undecane. A tandem 1,5- or 1,6-HAT-oxidation-nucleophilic cyclisation mechanism is proposed.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2009.05.049
URIhttp://hdl.handle.net/10261/211686
DOI10.1016/j.tet.2009.05.049
Identifiersdoi: 10.1016/j.tet.2009.05.049
issn: 0040-4020
Appears in Collections:(IPNA) Artículos
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