Asymmetric Grignard Cross-Coupling Reaction Using an N–Ar Axially Chiral Mimetic-Type Ligand

Abstract

A novel chiral ligand mimicking N–Ar axial chirality, (S)-N-[2-(diphenylphosphanyl)naphthalene-1-yl]-2-(piperidinylmethyl)piperidine, was found to exhibit good enantioselectivity (up to 80% ee) in the asymmetric cross-coupling reaction of 1-phenylethylmagnesium chloride with β-bromostyrene derivatives. To the best of our knowledge, the results are the third best enantioselectivity in the reported literature. Additionally, this type ligand is appealing, because it allows the synthesis of a wide variety of analogues.