Synthesis and chiral discrimination of cyclic aromatic amides and the determination of their absolute configuration by TD-DFT calculations |
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Authors: | Kosuke Katagiri Takashi Ikeda Atsuya Muranaka Masanobu Uchiyama Masahide Tominaga Isao Azumaya |
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Institution: | 1. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan;2. Advanced Elements Chemistry Laboratory, The Institute of Physical and Chemical Research, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan |
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Abstract: | 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. |
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