Synthesis and chiral recognition ability of O-phenyl ethylphosphonothioic acid with a conformationally flexible phenoxy group for CH/π interaction
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概要
- 論文の詳細を見る
Enantiopure O-phenyl ethylphosphonothioic acid (1) was easily obtained by the enantioseparation of racemic 1, which was prepared from commercially available phosphorothioic trichloride through four steps. Enantiopure 1 was found to show an excellent chiral recognition ability for various 1-arylethylamine derivatives during the diastereomeric salt formation. Especially, enantiopure 1 could recognize the chirality of o- and m-substituted 1-arylethylamine derivatives, of which the chirality is generally difficult to be distinguished by conventional resolving agents. The X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that the conformation of the phenoxy group in enantiopure 1 could flexibly change in the diastereomeric salt crystals and that the excellent chiral recognition ability of enantiopure 1 resulted from the effective CH/π interaction of the phenoxy phenyl group.
- Elsevierの論文
- 2006-03-20
著者
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SAIGO Kazuhiko
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
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MAEDA Jin
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo
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Maeda Jin
Department Of Chemistry And Biotechnology Graduate School Of Engineering The University Of Tokyo
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Kobayashi Yuka
Department Of Chemistry And Biotechnology Graduate School Of Engineering The University Of Tokyo
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