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Intramolecular 1,5-hydrogen atom transfer reaction promoted by phosphoramidyl and carbamoyl radicals: synthesis of 2-amino-C-glycosides

AuthorsFrancisco, Cosme G. ; Herrera, Antonio J. ; Martín, Ángeles ; Pérez-Martín, Inés ; Suárez, Ernesto
Issue Date4-Jul-2007
CitationTetrahedron Letters 48(36): 6384-6388 (2007)
AbstractThe preparation of 2-amino-C-glycosides of the hexahydro-2H-furo[3,2-b]pyrrole and octahydropyrano[3,2-b]pyrrole systems is described. A tandem 1,5-hydrogen atom transfer–radical oxidation–nucleophilic cyclisation mechanism is proposed for the intramolecular hydrogen atom transfer reaction promoted by carbamoyl and phosphoramidyl radicals employing hipervalent iodine oxidants.
Description5 páginas, 2 tablas, 3 esquemas.
Full characterisation of compounds and experimental details. Supplementary data (13 pages) available at: http://dx.doi.org/10.1016/ j.tetlet.2007.06.152
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2007.06.152
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