Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary.
Chirality. 2010 Jul;22(7):699-705. doi: 10.1002/chir.20821.
A simple, efficient, and economical method based on the combination of the exceptional behavior of o,o'-dibenzoyl- or o,o'-di-p-toluyl-(2R,3R)-tartaric acid in chiral recognition processes, and the coordination ability of calcium or magnesium ion was developed for the resolution of phospholene oxides 1. The calcium or magnesium salt of (-)-o,o'-dibenzoyl-(2R,3R)-tartaric acid 2,4-6 or calcium hydrogen (-)-o,o'-di-p-toluyl-(2R,3R)-tartrate 3 may form crystalline diastereomeric coordination complexes with the appropriate antipode of substituted 3-phospholene oxides 1 that makes possible efficient resolutions. Optically active phospholene oxides 1 were prepared directly by simply crystallization and digestion of the corresponding diastereomeric complexes so formed. Thermal behavior of the crystalline diastereomeric complexes was studied by simultaneous TG/DTA. The novel method may be of more general value in respect of the resolution of tertiary phosphine oxides.
基于邻苯二甲酰基或邻对甲苯酰基-（2R,3R）-酒石酸在手性识别过程中的特殊行为，以及钙或镁离子的配位能力，开发了一种简单、高效、经济的方法，用于拆分膦氧化物 1。（-）-邻苯二甲酰基-（2R,3R）-酒石酸 2,4-6 的钙或镁盐或钙氢（-）-邻对甲苯酰基-（2R,3R）-酒石酸 3 可能与取代的 3-磷杂环氧化物 1 的合适对映体形成结晶的非对映异构体配位配合物，从而实现有效的拆分。通过简单地结晶和消化形成的相应非对映异构体配合物，可以直接制备光学活性的磷杂环氧化物 1。通过同步 TG/DTA 研究了结晶非对映异构体配合物的热行为。该新方法在手性磷酸酯氧化物的拆分方面可能具有更普遍的价值。
