(+/-)-Piperidine-2-carboxylic acid ((+/-)-pipecolic acid) has been res
olved by the fractional crystallisation of diastereomeric palladium(II
) complexes containing orthometallated (S)-(-)-1-[1-dimethylamino)ethy
l]naphthalene. The enantiomers of the acid were liberated from the ind
ividual configurationally homogeneous diastereomers of the complex in
high yield with [alpha](D)+/-26.0 (c 1.00, H2O). The crystal and molec
ular structures of both diastereomers of the complex have been determi
ned.