Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols

Autores
Duran, Fernando Javier; Leman, Loïc; Ghini, Alberto Antonio; Burton, Gerardo; Dauban, Philippe; Dodd, Robert H.
Año de publicación
2002
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
(Matrix presented) Olefinic sulfamates derived from primary and secondary alcohols undergo intramolecular copper-catalyzed aziridination in the presence of iodosylbenzene to afford novel bicyclic fused aziridines. The latter were opened by various nucleophiles to give the corresponding substituted cyclic sulfamates, which in turn reacted, after nitrogen activation, with a second nucleophile at the carbon atom bearing the oxygen atom. Concomitant removal of the sulfonyloxy moiety thus gave access to polysubstituted amines.
Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Leman, Loïc. Centre National de la Recherche Scientifique; Francia
Fil: Ghini, Alberto Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Dauban, Philippe. Centre National de la Recherche Scientifique; Francia
Fil: Dodd, Robert H.. Centre National de la Recherche Scientifique; Francia
Materia
AZIRIDINES
CATALISYS
INTRAMOLECULAR
COPPER
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/86459
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcoholsDuran, Fernando JavierLeman, LoïcGhini, Alberto AntonioBurton, GerardoDauban, PhilippeDodd, Robert H.AZIRIDINESCATALISYSINTRAMOLECULARCOPPERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1(Matrix presented) Olefinic sulfamates derived from primary and secondary alcohols undergo intramolecular copper-catalyzed aziridination in the presence of iodosylbenzene to afford novel bicyclic fused aziridines. The latter were opened by various nucleophiles to give the corresponding substituted cyclic sulfamates, which in turn reacted, after nitrogen activation, with a second nucleophile at the carbon atom bearing the oxygen atom. Concomitant removal of the sulfonyloxy moiety thus gave access to polysubstituted amines.Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Leman, Loïc. Centre National de la Recherche Scientifique; FranciaFil: Ghini, Alberto Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Dauban, Philippe. Centre National de la Recherche Scientifique; FranciaFil: Dodd, Robert H.. Centre National de la Recherche Scientifique; FranciaAmerican Chemical Society2002-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/86459Duran, Fernando Javier; Leman, Loïc; Ghini, Alberto Antonio; Burton, Gerardo; Dauban, Philippe; et al.; Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols; American Chemical Society; Organic Letters; 4; 15; 7-2002; 2481-24831523-7060CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol0200899info:eu-repo/semantics/altIdentifier/doi/10.1021/ol0200899info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:06:12Zoai:ri.conicet.gov.ar:11336/86459instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:06:12.387CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
spellingShingle Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
Duran, Fernando Javier
AZIRIDINES
CATALISYS
INTRAMOLECULAR
COPPER
title_short Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_full Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_fullStr Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_full_unstemmed Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
title_sort Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols
dc.creator.none.fl_str_mv Duran, Fernando Javier
Leman, Loïc
Ghini, Alberto Antonio
Burton, Gerardo
Dauban, Philippe
Dodd, Robert H.
author Duran, Fernando Javier
author_facet Duran, Fernando Javier
Leman, Loïc
Ghini, Alberto Antonio
Burton, Gerardo
Dauban, Philippe
Dodd, Robert H.
author_role author
author2 Leman, Loïc
Ghini, Alberto Antonio
Burton, Gerardo
Dauban, Philippe
Dodd, Robert H.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv AZIRIDINES
CATALISYS
INTRAMOLECULAR
COPPER
topic AZIRIDINES
CATALISYS
INTRAMOLECULAR
COPPER
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv (Matrix presented) Olefinic sulfamates derived from primary and secondary alcohols undergo intramolecular copper-catalyzed aziridination in the presence of iodosylbenzene to afford novel bicyclic fused aziridines. The latter were opened by various nucleophiles to give the corresponding substituted cyclic sulfamates, which in turn reacted, after nitrogen activation, with a second nucleophile at the carbon atom bearing the oxygen atom. Concomitant removal of the sulfonyloxy moiety thus gave access to polysubstituted amines.
Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Leman, Loïc. Centre National de la Recherche Scientifique; Francia
Fil: Ghini, Alberto Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Burton, Gerardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Dauban, Philippe. Centre National de la Recherche Scientifique; Francia
Fil: Dodd, Robert H.. Centre National de la Recherche Scientifique; Francia
description (Matrix presented) Olefinic sulfamates derived from primary and secondary alcohols undergo intramolecular copper-catalyzed aziridination in the presence of iodosylbenzene to afford novel bicyclic fused aziridines. The latter were opened by various nucleophiles to give the corresponding substituted cyclic sulfamates, which in turn reacted, after nitrogen activation, with a second nucleophile at the carbon atom bearing the oxygen atom. Concomitant removal of the sulfonyloxy moiety thus gave access to polysubstituted amines.
publishDate 2002
dc.date.none.fl_str_mv 2002-07
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/86459
Duran, Fernando Javier; Leman, Loïc; Ghini, Alberto Antonio; Burton, Gerardo; Dauban, Philippe; et al.; Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols; American Chemical Society; Organic Letters; 4; 15; 7-2002; 2481-2483
1523-7060
CONICET Digital
CONICET
url http://hdl.handle.net/11336/86459
identifier_str_mv Duran, Fernando Javier; Leman, Loïc; Ghini, Alberto Antonio; Burton, Gerardo; Dauban, Philippe; et al.; Intramolecular Phl=O mediated copper-catalyzed aziridination of unsaturated sulfamates: A new direct access to polysubstituted amines from simple homoallylic alcohols; American Chemical Society; Organic Letters; 4; 15; 7-2002; 2481-2483
1523-7060
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol0200899
info:eu-repo/semantics/altIdentifier/doi/10.1021/ol0200899
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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