ENANTIOSELECTIVE CATALYSIS .13. PREPARATIVE AND STRUCTURAL CHEMISTRY OF CHIRAL 3-(DIPHENYLPHOSPHANYL)PYRROLIDINES AND THEIR PALLADIUM(II) COMPLEXES

The preparation of both enantiomers of 3-diphenylphosphanylpyrrolidine (2) and several N-substituted derivatives together with two Pd-II com plexes of this ligand is reported. From L-malic acid and L-hydroxyprol ine both enantiomers of 3-hydroxypyrrolidine are prepared without any problems due to epimerization. KPPh(2) in the presence of LiCl is show n to be the most effective reagent for the synthesis of 2. The reporte d X-ray structure determinations of PDI2 complexes show a rather rigid bicyclic hetero-norbornane skeleton. The flexibility of the other par ts of the molecules is obvious in several polymorphs revealed by this method. This polymorphism is additionally investigated by a P-31-CP-MA S study. From solution H-1-, C-13- and P-31-NMR studies it is conclude d that the bicyclic hetero-norbornane skeleton is retained in solution .