Catalytic stereoselective alkene aziridination with sulfonimidamides

Authors
Robert-Peillard, Fabien; Di Chenna, Pablo Hector; Liang, Chungen; Lescot, Camille; Collet, Florence; Dodd, Robert H.; Dauban, Philippe
Publication Year
2010
Language
English
Format
article
Status
Published version
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.
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
Subject
AZIRIDINE
ALKENE
NITRENE
COPPER
HYPERVALENT IODINE
STEREOSELECTIVITY
Otras Ciencias Químicas
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Restricted access
License
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/69386