Chiral beta-phosphino sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions

The first attempt to use chiral beta-phosphino sulfoxides as chiral ligands was successfully accomplished in a palladium-catalyzed asymmetric allylic alkylation and amination, providing extremely high enantioselectivity with chiral 2-(diphenylphosphino)phenyl 2-methoxy-1-naphthyl sulfoxide. The stru cture of the intermediary palladium complex chelated by the ligand was dete rmined by the X-ray crystallographic analysis. The mechanism for the asymme tric induction is proposed on the basis of the stereochemical results obtai ned. (C) 1999 Elsevier Science Ltd. All rights reserved.