Synthesis and chiral discrimination of cyclic aromatic amides and the determination of their absolute configuration by TD-DFT calculations

Novel chiral cyclic molecules composed of aromatic triamides were constructed in modest yield from 4-N-(4'-methoxybenzyl)amino-3-decyloxybenzoic acid using dichlorotriphenylphosphorane, because of the preorganized component of the tertiary benzanilide moieties. A racemic mixture of two diastereomers, syn and anti conformers of cyclic aromatic triamides, was resolved into enantiomers by HPLC using a preparative chiral column. The absolute configuration of each enantiomer in both diastereomers was determined by comparison of the time-dependent density functional theory (TD-DFT) calculated circular dichroic (CD) spectra with the experimentally derived CD spectra recorded on each sample. (C) 2009 Elsevier Ltd. All rights reserved.