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Intramolecular hydrogen abstraction promoted by N-radicals: synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems

AuthorsFrancisco, Cosme G. ; Herrera, Antonio J. ; Suárez, Ernesto
Issue Date6-Oct-2000
CitationTetrahedron Asymmetry 11(19): 3879-3882 (2000)
AbstractHomochiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems can be synthesized by reaction of specifically protected phosphoramidate derivatives of carbohydrates with (diacetoxyiodo)benzene or iodosylbenzene and iodine. The reaction mechanism goes through homolytic fragmentation of a hypothetical iodoamide intermediate. The N-radicals so generated participate in an intramolecular hydrogen abstraction reaction (IHA) to give the aforementioned bicycles.
Description4 pages, 1 table, 1 scheme.
Publisher version (URL)http://dx.doi.org/10.1016/S0957-4166(00)00364-5
Appears in Collections:(IPNA) Artículos
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