アミノ酸ユニットの会合特性に基づく不斉構造誘起

概要

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Introduction of amino acid units into a ferrocene or 2, 6-pyridinedicarboxamide scaffold has been demonstrated to form an ordered structure in both solid and solution states. Conformational enantiomerization through chirality organization was achieved. The single-crystal X-ray structure determination of the ferrocene bearing the podand chiral dipeptide chains (-L-Ala-L-Pro-OEt) and the D-derivative revealed two <I>C</I><SUB>2</SUB>-symmetrical intramolecular interchain hydrogen bondings to induce the chirality organized structures. The molecular structures of the L- and D-isomer are in a good mirror image relationship based on conformational enantiomers. The single-crystal X-ray structure determination of the chiral 2, 6-pyridinedicarboxamide bearing the podand L-histidyl moieties and the D-derivative confirmed a left- and right-handed helical conformation, respectively, through intramolecular hydrogen bonding and chirality of the podand histidyl moieties. The propensity to form the chiral helicity appears to be controlled by the configuration of the histidyl α-carbon atoms. These chiral 2, 6-pyridinedicarboxamides were found to induce the chiral complexation.
社団法人有機合成化学協会の論文
2001-12-01