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Synthesis of a New Ligand for Metal Assembly to a Selective Receptor

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journal contribution
posted on 02.03.1999, 00:00 by Alan W. Schwabacher, Andrei D. Stefanescu, Atiq ur Rehman
Diarylphosphinic acid 2, bearing two ethylenediamine groups, was designed with the aim of assembly to form a hydrophobic cavity upon binding to metals. The new ligand was prepared in optically active form from phenylalanine by an efficient sequence which required chromatography only for the P−C bond forming steps. Versatile intermediates in the synthesis are described. Complexes of this ligand with Zn2+ were shown to bind closely related aromatic guests bearing anionic tethered groups with 1000-fold discrimination.