Asymmetric cyclopropanation and aziridination reactions of olefins catalyzed by Cu(I)-binaphthyldiimine complexes

The chiral Cu(I)-N,N'-bis(2,6-dichlorobenzylidene)-1,1'-binaphthyl-2,2'-diamine complex was found to be an efficient catalyst for asymmetric cyclopropanation and aziridination reactions of olefins with l-menthyl diazoacetate and [N(p-tolylsulfonyl)imino]phenyliodinane, respectively. Among mono- and disubstituted olefins, 1,1-diarylethylenes showed extremely high enantioselectivities (up to 98% ee) in the cyclopropanation reactions in the presence of a chiral Cu(I)-catalyst (2 mol%). In the case of aziridination reactions catalyzed by the same Cu(I)-catalyst (10 mol%), the reaction of traps-substituted 3-aryl-2-propenoates and 1-substituted trans-3-aryl-2-propen-1-ones showed satisfactory results in term of the enantioselectivities (up to 98% ee).