Rigidified tripodal chiral ligands in the asymmetric recognition of amino compounds

Chiral rigidified piperidine and quinuclidine analogues of tris(2-pyridylmethyl)amine (TPA) derivatives were examined for asymmetric recognition of amino compounds by cyclic voltammetry and fluorescence. A Cu(II) complex of a piperidine analogue discriminated the enantiomers of some chiral amines and amino alcohols, giving differences in electrochemical potential for diastereomeric complexes. Protonated piperidine and quinuclidine analogues were able to differentiate the two enantiomers of certain amino alcohols by fluorescence spectroscopy. The quinuclidine analogue gave a 3-fold difference in response to the two enantiomers of phenyglycinol. (c) 2005 Wiley-Liss, Inc.