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We carried out systematic studies on the preferential and diastereomeric crystallizations with the aid of X-ray crystallographic analyses and found that there is high correlation in molecular length between a target racemate and a derivatizing/resolving agent. On the basis of the results, we proposed relative molecular length and CH/π rules. The rules were applied to the development of non-natural enantiopure compounds, which were highly useful in asymmetric syntheses, chiral polyamide synthesis, and so on. Recent results concerned with the enantioseparation by phosphonothioic and phosphinothioic acids and with the asymmetric synthesis of phosphorothioates are also described.

yūki gōsei kagaku kyōkaishi/yuuki gousei kagaku kyoukaishi

Elucidation of Chiral Recognition Mechanism During Preferential and Diastereomeric Crystallizations, and Application to the Development and Utilization of Artificial Enantiopure Compounds