Enantioselective Allylic Substitution Using a Novel (Phosphino-α-d-glucopyrano-oxazoline)palladium Catalyst

Abstract

A novel enantiomerically pure 2-[2-(diphenylphosphino)phenyl]-4,5-(2-deoxy-α-d-glucopyrano)-oxazoline ligand (6) was prepared from glucosamine (1). The stereodifferentiating potential of the ligand 6 was demonstrated in palladium-catalyzed intermolecular allylic substitutions of symmetrically and non-symmetrically substituted allyl acetates which give products in high yields and high enantioselectivity (up to 98% ee).