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

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 (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.

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Bibliographic Details
Main Authors: Martín, Ángeles, Pérez-Martín, Inés, Suárez, Ernesto
Other Authors: Consejo Superior de Investigaciones Científicas (España)
Format: artículo biblioteca
Published: Elsevier 2009-08-01
Subjects:Intramolecular hydrogen atom transfer, N-Radical, Diacetoxyiodo, Benzene, N-Phosphoramidate, N-Cyanamide,
Online Access:http://hdl.handle.net/10261/211686
http://dx.doi.org/10.13039/501100008737
http://dx.doi.org/10.13039/501100003339
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spelling dig-ipna-es-10261-2116862020-12-09T15:59:55Z Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems Martín, Ángeles Pérez-Martín, Inés Suárez, Ernesto Consejo Superior de Investigaciones Científicas (España) Dirección General de Investigación Científica y Técnica, DGICT (España) Intramolecular hydrogen atom transfer N-Radical Diacetoxyiodo Benzene N-Phosphoramidate N-Cyanamide 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. 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. 2020-05-20T08:14:02Z 2020-05-20T08:14:02Z 2009-08-01 2020-05-20T08:14:02Z artículo http://purl.org/coar/resource_type/c_6501 doi: 10.1016/j.tet.2009.05.049 issn: 0040-4020 Tetrahedron 65(31): 6147-6155 (2009) http://hdl.handle.net/10261/211686 10.1016/j.tet.2009.05.049 http://dx.doi.org/10.13039/501100008737 http://dx.doi.org/10.13039/501100003339 Postprint http://dx.doi.org/10.1016/j.tet.2009.05.049 Sí open Elsevier
institution IPNA ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-ipna-es
tag biblioteca
region Europa del Sur
libraryname Biblioteca del IPNA España
topic Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
spellingShingle Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
Martín, Ángeles
Pérez-Martín, Inés
Suárez, Ernesto
Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
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.
author2 Consejo Superior de Investigaciones Científicas (España)
author_facet Consejo Superior de Investigaciones Científicas (España)
Martín, Ángeles
Pérez-Martín, Inés
Suárez, Ernesto
format artículo
topic_facet Intramolecular hydrogen atom transfer
N-Radical
Diacetoxyiodo
Benzene
N-Phosphoramidate
N-Cyanamide
author Martín, Ángeles
Pérez-Martín, Inés
Suárez, Ernesto
author_sort Martín, Ángeles
title Synthesis of oxa-aza spirobicycles by intramolecular hydrogen atom transfer promoted by N-radicals in carbohydrate systems
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
publisher Elsevier
publishDate 2009-08-01
url http://hdl.handle.net/10261/211686
http://dx.doi.org/10.13039/501100008737
http://dx.doi.org/10.13039/501100003339
work_keys_str_mv AT martinangeles synthesisofoxaazaspirobicyclesbyintramolecularhydrogenatomtransferpromotedbynradicalsincarbohydratesystems
AT perezmartinines synthesisofoxaazaspirobicyclesbyintramolecularhydrogenatomtransferpromotedbynradicalsincarbohydratesystems
AT suarezernesto synthesisofoxaazaspirobicyclesbyintramolecularhydrogenatomtransferpromotedbynradicalsincarbohydratesystems
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