Iron-Catalyzed Highly Enantioselective Addition of Silyl Enol Ethers to α,ß-Unsaturated 2-Acyl Imidazoles.

A chiral FeII(N4) complex (N4 = (R,R)-N,N'-bis(2-isopropylquinolin-8-yl)-1,2-diphenylethane-1,2-diamine) was developed for the asymmetric conjugate addition of silyl enol ethers, including both acyclic ones and cyclohexenone-derived ones, to α,ß-unsaturated 2-acyl imidazoles. This FeII complex is an effective chiral Lewis acid and was applied in the synthesis of an array of chiral 1,5-dicarbonyl synthons and cyclohexenone derivatives with high yields and enantioselectivities (up to 99% ee).