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

AuthorsFreire, Raimundo ; Martín, Ángeles ; Pérez-Martín, Inés ; Suárez, Ernesto
Issue Date9-Jun-2002
CitationTetrahedron Letters 43(29): 5113-5116 (2002)
AbstractThe preparation of 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 ring systems by 1,6- and 1,7-hydrogen atom transfer promoted by phosphoramidyl radicals in carbohydrate models is described. The N-radicals are generated by reaction of dibenzyl phosphoramidate derivatives of C-glycosides with (diacetoxyiodo)benzene and iodine through an homolytic fragmentation of iodoamide intermediates.
Description4 pages, 1 table, 2 schemes.-- Printed version published Jul 15, 2002.
Publisher version (URL)http://dx.doi.org/10.1016/S0040-4039(02)00983-8
Appears in Collections:(IPNA) Artículos
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