Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems

The nitrogen-centred radical generated by reaction of an N-phosphoramidate or N-cyanamide, attached to a tri- or tetramethylene tether extended from the C-1 of a carbohydrate, with (diacetoxyiodo)benzene (DIB) and iodine can undergo a regio- and stereoselective intramolecular hydrogen atom transfer...

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Detalles Bibliográficos
Autores: Martín, Ángeles, Pérez-Martín, Inés, Suárez, Ernesto
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2009
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/211686
Acceso en línea:http://hdl.handle.net/10261/211686
Access Level:acceso abierto
Palabra clave:Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
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spelling Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systemsMartín, ÁngelesPérez-Martín, InésSuárez, ErnestoIntramolecular hydrogen atom transferN-RadicalDiacetoxyiodoBenzeneN-PhosphoramidateN-CyanamideThe nitrogen-centred radical generated by reaction of an N-phosphoramidate or N-cyanamide, attached to a tri- or tetramethylene tether extended from the C-1 of a carbohydrate, with (diacetoxyiodo)benzene (DIB) and iodine can undergo a regio- and stereoselective intramolecular hydrogen atom transfer (HAT) reaction to furnish four different oxa-azaspirobicyclic systems: 1-oxa-6-azaspiro[4.4]nonane, 1-oxa-6-azaspiro[4.5]decane, 6-oxa-1-azaspiro[4.5]decane and 1-oxa-7-azaspiro[5.5]undecane. A tandem 1,5- or 1,6-HAT-oxidation-nucleophilic cyclisation mechanism is proposed.This work was supported by the research programmes BQU2000-0650 and BQU2001-1665 of the Dirección General de Investigación Científica y Técnica, Spain. I.P.-M. thanks the I3P-CSIC programme for a fellowship.ElsevierConsejo Superior de Investigaciones Científicas (España)Dirección General de Investigación Científica y Técnica, DGICT (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2020202020092020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/211686reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1016/j.tet.2009.05.049Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2116862026-05-22T06:33:51Z
dc.title.none.fl_str_mv Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
title Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
spellingShingle Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
Martín, Ángeles
Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
title_short Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
title_full Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
title_fullStr Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
title_full_unstemmed Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
title_sort Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
dc.creator.none.fl_str_mv Martín, Ángeles
Pérez-Martín, Inés
Suárez, Ernesto
author Martín, Ángeles
author_facet Martín, Ángeles
Pérez-Martín, Inés
Suárez, Ernesto
author_role author
author2 Pérez-Martín, Inés
Suárez, Ernesto
author2_role author
author
dc.contributor.none.fl_str_mv Consejo Superior de Investigaciones Científicas (España)
Dirección General de Investigación Científica y Técnica, DGICT (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
topic Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
description The nitrogen-centred radical generated by reaction of an N-phosphoramidate or N-cyanamide, attached to a tri- or tetramethylene tether extended from the C-1 of a carbohydrate, with (diacetoxyiodo)benzene (DIB) and iodine can undergo a regio- and stereoselective intramolecular hydrogen atom transfer (HAT) reaction to furnish four different oxa-azaspirobicyclic systems: 1-oxa-6-azaspiro[4.4]nonane, 1-oxa-6-azaspiro[4.5]decane, 6-oxa-1-azaspiro[4.5]decane and 1-oxa-7-azaspiro[5.5]undecane. A tandem 1,5- or 1,6-HAT-oxidation-nucleophilic cyclisation mechanism is proposed.
publishDate 2009
dc.date.none.fl_str_mv 2009
2020
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/211686
url http://hdl.handle.net/10261/211686
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1016/j.tet.2009.05.049
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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