2024-03-29T09:22:52Z
https://repository.dl.itc.u-tokyo.ac.jp/oai
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2022-12-19T03:40:57Z
6:18:19
9:10:11
Synthesis and chiral recognition ability of O-phenyl ethylphosphonothioic acid with a conformationally flexible phenoxy group for CH/π interaction
Saigo, Kazuhiko
105803
Kobayashi, Yuka
105804
Maeda, Jin
105805
Morisawa, Fumi
105806
application/pdf
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.
journal article
Elsevier
2006-03-20
application/pdf
Tetrahedron: Asymmetry
6
17
967
974
09574166
https://repository.dl.itc.u-tokyo.ac.jp/record/57/files/26_Elsevier_w.pdf
eng
info:doi/10.1016/j.tetasy.2006.03.009
http://www.elsevier.com/locate/issn/09574166