Chiral ferrocenyl amidophosphine ligand for highly enantioselective addition of diethylzinc to N-diphenylphosphinoylimines

Abstract

The asymmetric addition of diethylzinc to N-diphenylphosphinoylimines afforded N-diphenylphosphinoylamides with enantioselectivity of up to 90% ee in the presence of a catalytic amount of chiral ligand ( S)- N-ferrocenoyl-2-[(diphenylphosphino)methyl]-pyrrolidine 13 (7 mol %) and Cu(OTf) 2 (15 mol %). The remarkable improvement of enantioselectivities, as compared with the same type of chiral ligand 6, could be explained by the unique structure of ferrocenyl amidophosphine ligand combining with the reactive intermediate of this addition reaction.