Sulfonimidamides: efficient chiral iminoiodane precursors for diastereoselective copper-catalyzed aziridination of olefins.
N-(p-Toluenesulfonyl)-p-toluenesulfonimidamide reacts with iodosylbenzene to afford in situ a chiral iminoiodane. The latter gives, in the presence of a copper(I) catalyst, a nitrene that is very efficiently transferred under stoichiometric conditions to a variety of alkenes with diastereoselectivities up to 60%. [reaction: see text]
Di Chenna
Pablo H
PH
Institut de Chimie des Substances Naturelles, CNRS, avenue de la terrasse, F-91198 Gif-sur-Yvette, France.
Robert-Peillard
Fabien
F
Dauban
Philippe
P
Dodd
Robert H
RH