Catalytic stereoselective alkene aziridination with sulfonimidamides |
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Authors: | Fabien Robert-Peillard Pablo H. Di Chenna Chungen Liang Camille Lescot Florence Collet Robert H. Dodd Philippe Dauban |
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Affiliation: | Institut de Chimie des Substances Naturelles, UPR 2301 CNRS, Centre de Recherche de Gif-sur-Yvette, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France |
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Abstract: | 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. |
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