info:eu-repo/semantics/article
Catalytic stereoselective alkene aziridination with sulfonimidamides
Fecha
2010-06Registro en:
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
Autor
Robert-Peillard, Fabien
Di Chenna, Pablo Hector
Liang, Chungen
Lescot, Camille
Collet, Florence
Dodd, Robert H.
Dauban, Philippe
Resumen
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.