Stereochemistry of the reaction of an optically active π-allylpalladium complex with nucleophiles

The stereochemistry of the reaction of π-allylpalladium complexes with nucleophiles has been elucidated using optically active (–)-(1S,2R,3R)-di-µ-chloro-bis(1-methyl-3-phenyl-π-allyl)dipalladium(II); dimethyl sodiomalonate and dimethylamine attack a carbon atom of the π-allyl ligand from the side opposite to the palladium (inversion), and phenyl and allyl Grignard reagents attack the π-allyl carbon atom from the same side as the palladium (retention).