An N–Ar axially chiral mimetic. A new approach to ligand design for asymmetric catalysis

A new-type chiral ligand, (S)-N-[2-(diphenylphosphino)naphthyl]-2-(pyrrolidinylmethyl)piperidine mimicking N–Ar axial chirality, has been developed. This chiral ligand was found to exhibit 99% ee with the use of (E)-1,3-diphenyl-2-propenyl acetate as the standard substrate, and achieved slightly better results than the Pfaltz and Trost ligands with the use of (E)-1-phenyl-3-trimethylsilyl-2-propenyl acetate as the substrate, in the palladium-catalyzed asymmetric allylic substitution.