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

Abstract

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. © 2002 Elsevier Science Ltd. All rights reserved.