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

descriptionPublicationkeyboard_double_arrow_right Article 01 Oct 2000 Spain English Publisher:Elsevier BVJournal:Tetrahedron: Asymmetry, volume 11, pages 3,879-3,882 (issn: 0957-4166,

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Authors: Francisco, Cosme G.; Herrera, Antonio J.; Suárez, Ernesto;

doi: 10.1016/s0957-4166(00)00364-5

handle: 10261/17234

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

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Abstract

Homochiral 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.

This work was supported by Investigation Programme PB96-1461 of the Direction General de Investigación Científica y Técnica. A.J.H. thanks the Ministerio de Educación y Ciencia, Spain, for a fellowship.

4 pages, 1 table, 1 scheme.

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Spain

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Spanish National Research Council
Spain

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