ENANTIOSELECTIVE ALLYLIC SUBSTITUTIONS CATALYZED BY [(HYDROXYALKYL)PYRIDINOOXAZOLINE]PALLADIUM AND [(ALKOXYALKYL)PYRIDINOOXAZOLINE]PALLADIUM COMPLEXES

Highly enantioselective (up to >99% eel palladium-catalyzed substituti on of rac-3-diphenyl-2-propenyl acetate with dimethyl malonate as nucl eophile was achieved using -hydroxyalkyl)-6-(4,5-dihydro-2-oxazolyl)py ridines and 1-alkoxyalkyl)-6-(4,5-dihydro-2-oxazolyl)pyridines as liga nds for palladium. The selectivity was found to be highly dependent on the nature of the substituents on the ligand and on the relative conf iguration of the two stereogenic centers present in the ligand. The re sults are discussed in terms of the conformation of the ligands in the intermediate pi-allylpalladium complexes.