Catalytic stereoselective alkene aziridination with sulfonimidamides

Autores
Robert-Peillard, Fabien; Di Chenna, Pablo Hector; Liang, Chungen; Lescot, Camille; Collet, Florence; Dodd, Robert H.; Dauban, Philippe
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Diastereoselective copper-catalyzed alkene aziridination has been investigated using chiral nitrenes generated from sulfonimidamides in the presence of an iodine(III) oxidant. Starting from a stoichiometric amount of the substrates, the corresponding aziridines were isolated with excellent yields of up to 96%. Good levels of asymmetric induction were obtained in the case of electron-poor olefins, with an optimal de of 94% being reached starting from tert-butyl acrylate. Matching and mismatching effects were also observed upon the use of chiral copper catalysts for the aziridination of styrene.
Fil: Robert-Peillard, Fabien. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Di Chenna, Pablo Hector. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Liang, Chungen. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Lescot, Camille. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Collet, Florence. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Dodd, Robert H.. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Dauban, Philippe. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; Francia
Materia
Aziridine
Alkene
Nitrene
Copper
Hypervalent Iodine
Stereoselectivity
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:11336/69386
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/69386
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Catalytic stereoselective alkene aziridination with sulfonimidamidesRobert-Peillard, FabienDi Chenna, Pablo HectorLiang, ChungenLescot, CamilleCollet, FlorenceDodd, Robert H.Dauban, PhilippeAziridineAlkeneNitreneCopperHypervalent IodineStereoselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Diastereoselective copper-catalyzed alkene aziridination has been investigated using chiral nitrenes generated from sulfonimidamides in the presence of an iodine(III) oxidant. Starting from a stoichiometric amount of the substrates, the corresponding aziridines were isolated with excellent yields of up to 96%. Good levels of asymmetric induction were obtained in the case of electron-poor olefins, with an optimal de of 94% being reached starting from tert-butyl acrylate. Matching and mismatching effects were also observed upon the use of chiral copper catalysts for the aziridination of styrene.Fil: Robert-Peillard, Fabien. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; FranciaFil: Di Chenna, Pablo Hector. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; FranciaFil: Liang, Chungen. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; FranciaFil: Lescot, Camille. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; FranciaFil: Collet, Florence. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; FranciaFil: Dodd, Robert H.. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; FranciaFil: Dauban, Philippe. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; FranciaPergamon-Elsevier Science Ltd2010-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/69386Robert-Peillard, Fabien; Di Chenna, Pablo Hector; Liang, Chungen; Lescot, Camille; Collet, Florence; et al.; Catalytic stereoselective alkene aziridination with sulfonimidamides; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 21; 11-12; 6-2010; 1447-14570957-4166CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0957416610001874info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2010.03.032info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:35:14Zoai:ri.conicet.gov.ar:11336/69386instacron: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:34982025-11-12 09:35:15.296CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Catalytic stereoselective alkene aziridination with sulfonimidamides
title Catalytic stereoselective alkene aziridination with sulfonimidamides
spellingShingle Catalytic stereoselective alkene aziridination with sulfonimidamides
Robert-Peillard, Fabien
Aziridine
Alkene
Nitrene
Copper
Hypervalent Iodine
Stereoselectivity
title_short Catalytic stereoselective alkene aziridination with sulfonimidamides
title_full Catalytic stereoselective alkene aziridination with sulfonimidamides
title_fullStr Catalytic stereoselective alkene aziridination with sulfonimidamides
title_full_unstemmed Catalytic stereoselective alkene aziridination with sulfonimidamides
title_sort Catalytic stereoselective alkene aziridination with sulfonimidamides
dc.creator.none.fl_str_mv Robert-Peillard, Fabien
Di Chenna, Pablo Hector
Liang, Chungen
Lescot, Camille
Collet, Florence
Dodd, Robert H.
Dauban, Philippe
author Robert-Peillard, Fabien
author_facet Robert-Peillard, Fabien
Di Chenna, Pablo Hector
Liang, Chungen
Lescot, Camille
Collet, Florence
Dodd, Robert H.
Dauban, Philippe
author_role author
author2 Di Chenna, Pablo Hector
Liang, Chungen
Lescot, Camille
Collet, Florence
Dodd, Robert H.
Dauban, Philippe
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Aziridine
Alkene
Nitrene
Copper
Hypervalent Iodine
Stereoselectivity
topic Aziridine
Alkene
Nitrene
Copper
Hypervalent Iodine
Stereoselectivity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Diastereoselective copper-catalyzed alkene aziridination has been investigated using chiral nitrenes generated from sulfonimidamides in the presence of an iodine(III) oxidant. Starting from a stoichiometric amount of the substrates, the corresponding aziridines were isolated with excellent yields of up to 96%. Good levels of asymmetric induction were obtained in the case of electron-poor olefins, with an optimal de of 94% being reached starting from tert-butyl acrylate. Matching and mismatching effects were also observed upon the use of chiral copper catalysts for the aziridination of styrene.
Fil: Robert-Peillard, Fabien. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Di Chenna, Pablo Hector. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; Francia
Fil: Liang, Chungen. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Lescot, Camille. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Collet, Florence. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Dodd, Robert H.. Centre National de la Recherche Scientifique; Francia. Institut de Chimie des Substances Naturelles; Francia
Fil: Dauban, Philippe. Institut de Chimie des Substances Naturelles; Francia. Centre National de la Recherche Scientifique; Francia
description Diastereoselective copper-catalyzed alkene aziridination has been investigated using chiral nitrenes generated from sulfonimidamides in the presence of an iodine(III) oxidant. Starting from a stoichiometric amount of the substrates, the corresponding aziridines were isolated with excellent yields of up to 96%. Good levels of asymmetric induction were obtained in the case of electron-poor olefins, with an optimal de of 94% being reached starting from tert-butyl acrylate. Matching and mismatching effects were also observed upon the use of chiral copper catalysts for the aziridination of styrene.
publishDate 2010
dc.date.none.fl_str_mv 2010-06
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/11336/69386
Robert-Peillard, Fabien; Di Chenna, Pablo Hector; Liang, Chungen; Lescot, Camille; Collet, Florence; et al.; Catalytic stereoselective alkene aziridination with sulfonimidamides; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 21; 11-12; 6-2010; 1447-1457
0957-4166
CONICET Digital
CONICET
url http://hdl.handle.net/11336/69386
identifier_str_mv Robert-Peillard, Fabien; Di Chenna, Pablo Hector; Liang, Chungen; Lescot, Camille; Collet, Florence; et al.; Catalytic stereoselective alkene aziridination with sulfonimidamides; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 21; 11-12; 6-2010; 1447-1457
0957-4166
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://www.sciencedirect.com/science/article/pii/S0957416610001874
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetasy.2010.03.032
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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
_version_ 1848597179307917312
score 12.976206

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