Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems

Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems

6 pages, 2 tables, 3 schemes.-- PMID: 12558429 [PubMed].-- Printed version published Feb 7, 2003.

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Main Authors: Francisco, Cosme G., Herrera, Antonio J., Suárez, Ernesto
Other Authors: Dirección General de Investigación Científica y Técnica, DGICT (España)
Format: artículo biblioteca
Language:English
Published: American Chemical Society 2003-01-14
Online Access:http://hdl.handle.net/10261/16757
http://dx.doi.org/10.13039/501100008737
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spelling dig-ipna-es-10261-167572019-11-13T08:48:56Z Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems Francisco, Cosme G. Herrera, Antonio J. Suárez, Ernesto Dirección General de Investigación Científica y Técnica, DGICT (España) Ministerio de Educación y Ciencia (España) 6 pages, 2 tables, 3 schemes.-- PMID: 12558429 [PubMed].-- Printed version published Feb 7, 2003. Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo026314h The reaction of phenyl and benzyl amidophosphates and alkyl and benzyl carbamate derivatives of aminoalditols with (diacetoxyiodo)benzene or iodosylbenzene and iodine is a mild and selective procedure for the synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems under neutral conditions. This reaction can be considered to be an intramolecular N-glycosidation that goes through an intramolecular 1,5-hydrogen abstraction promoted by an N-amido radical followed by oxidation of the transient C-radical intermediate to an oxycarbenium ion. This methodology proved to be useful not only as a suitable strategy for the preparation of these bicyclic arrays but also for the selective oxidation of specific carbons of the carbohydrate skeleton, constituting a good procedure for the synthesis of protected N,O-uloses. This work was supported by the Investigation Programs no. BQU2000-0650 and BQU2001-1665 of the Dirección General de Investigación Científica y Técnica, Spain. A.J.H. thanks the Ministerio de Educación y Ciencia, Spain for fellowships. 2009-09-09T07:20:39Z 2009-09-09T07:20:39Z 2003-01-14 artículo http://purl.org/coar/resource_type/c_6501 Journal of Organic Chemistry 68(3): 1012-1017 (2003) 0022-3263 http://hdl.handle.net/10261/16757 10.1021/jo026314h http://dx.doi.org/10.13039/501100008737 en http://dx.doi.org/10.1021/jo026314h none 2373 bytes 381508 bytes text/plain application/pdf American Chemical Society
institution IPNA ES
collection DSpace
country España
countrycode ES
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databasecode dig-ipna-es
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region Europa del Sur
libraryname Biblioteca del IPNA España
language English
description 6 pages, 2 tables, 3 schemes.-- PMID: 12558429 [PubMed].-- Printed version published Feb 7, 2003.
author2 Dirección General de Investigación Científica y Técnica, DGICT (España)
author_facet Dirección General de Investigación Científica y Técnica, DGICT (España)
Francisco, Cosme G.
Herrera, Antonio J.
Suárez, Ernesto
format artículo
author Francisco, Cosme G.
Herrera, Antonio J.
Suárez, Ernesto
spellingShingle Francisco, Cosme G.
Herrera, Antonio J.
Suárez, Ernesto
Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
author_sort Francisco, Cosme G.
title Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
title_short Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
title_full Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
title_fullStr Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
title_full_unstemmed Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
title_sort intramolecular hydrogen abstraction reaction promoted by n-radicals in carbohydrates. synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems
publisher American Chemical Society
publishDate 2003-01-14
url http://hdl.handle.net/10261/16757
http://dx.doi.org/10.13039/501100008737
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AT herreraantonioj intramolecularhydrogenabstractionreactionpromotedbynradicalsincarbohydratessynthesisofchiral7oxa2azabicyclo221heptaneand8oxa6azabicyclo321octaneringsystems
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