The synthesis of immobilised chiral dendrimers

Abstract

A one pot synthetic approach to amino acid based chiral dendrimers was shown to give good yields for dendrimers with peptide linkages. Using this synthetic strategy, modification of the peripheral functionality is possible, as is the substitution of other amino acids to give mixed amino acid based dendrimers. Immobilization of our dendrimers was accomplished using a coupling method involving the carboxy derivatised dendrimers with an aminopropyl modified silica. The use of 2-ethoxy-1-ethoxy-1,2-dihydroquinoline in a one pot protocol gave enhanced reaction conditions from which silicas bearing very high levels of dendrimer were obtained. Solid state NMR analysis substantiated that the dendrimers were bound to the silica and that they appeared to be structurally intact. These immobilised chiral dendrimers constitute a new class of chiral stationary phases for use in HPLC.