Synthesis and resolution of an alpha-phenyl substituted ortho-palladated matrix

A novel ortho-palladated benzylaminate matrix bearing phenyl substituent at the alpha-carbon stereocenter was prepared in the racemic state by direct intramolecular palladation of tertiary diphenylmethylamine with palladium(I I) acetate; its structure and palladacycle conformation were determined by H-1 NMR studies of the mononuclear triphenylphosphine adduct. The resolutio n of the dimeric complex was performed via recrystallization of its diaster eomeric (S)-prolinate derivatives. The absolute configuration (R-C,R-C) of the enantiopure dimer thus obtained was determined by an X-ray diffraction investigation of the less soluble (R-C,SCSN)-diastereomer of its (S)-prolin ate adduct. (C) 1999 Elsevier Science Ltd. All rights reserved.