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

Authors
Francisco, CG Herrera, AJ Suarez, E
Citation
Cg. Francisco et al., Intramolecular hydrogen abstraction promoted by N-radicals: synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-osa-6-azabicyclo[3.2.1]octane ring systems, TETRAHEDR-A, 11(19), 2000, pp. 3879-3882
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
19
Year of publication
2000
Pages
3879 - 3882
Database
ISI
SICI code
0957-4166(20001006)11:19<3879:IHAPBN>2.0.ZU;2-9
Abstract
Homochiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]oc tane 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 f ragmentation of a hypothetical iodoamide intermediate. The N-radicals so ge nerated participate in an intramolecular hydrogen abstraction reaction (IHA ) to give the aforementioned bicycles. (C) 2000 Elsevier Science Ltd. Ail r ights reserved.