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タイトル: Synthesis and chiral recognition ability of O-phenyl ethylphosphonothioic acid with a conformationally flexible phenoxy group for CH/π interaction
著者: Saigo, Kazuhiko
Kobayashi, Yuka
Maeda, Jin
Morisawa, Fumi
発行日: 2006年3月20日
出版者: Elsevier
掲載誌情報: Tetrahedron: Asymmetry. 17(6), 2006.3, pp. 967-974
関連URI: http://www.elsevier.com/locate/issn/09574166
抄録: 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.
URI: http://hdl.handle.net/2261/6010
ISSN: 09574166
出現カテゴリ:014 自然科学
1134010 学術雑誌論文


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