Stereoselectivity in Reactions of Metal Complexes. Part XVII. Synthesis of Three New Optically Active Triamines: 2,6-Bismethyl>pyridine, 2,6-Bismethyl>pyridine, and 2,6-Bispyrro...

Article abstract of DOI:10.1002/hlca.19930760611

The three new optically active triamines derived from 2,6-bis(aminomethyl)pyridine, i.e. 2,6-bis1<<(2S)-2-(hydroxymethyl)pyrrolidin-1-yl>melhyl>pyridine (3a), 2,6-bis<<(2S)-2-(methoxymethyl)pyrrdlidin-1-yl>methyl>-pyridine (3b), and 2,6-bis<<(2S)-2-<(benzyloxy)methyl>pyrrolidin-1-yl>methyl>pyridine (3c), were synthesized.The equilibrium behaviour in solution and Cu(II) complex formation were studied by acidimetric titration and by UV/VIS and CD measurements.It was found that in aqueous solution, 3a can coordinate one of the CH2OH groups to Cu(II) upon deprotonation.X-Ray crystal structures were determined for the complexes ClO4*H2O, ClO4, and ClO4.In the solid state, coordination of both the OH and the alkoxy goups was observed, and the three ligands are pentacoordinated.