Macrocyclic compounds as chiral solvating agents for phosphinic, phosphonic, and phosphoric acids

Novel macrocyclic compounds, synthesized and used as chiral solvating agents for phosphinic, phosphonic, and phosphoric acids, are reported in this article. NMR (1H NMR and/or 31P NMR) studies demonstrate that these acids have large nonequivalent chemical shifts in the presence of these macrocyclic compounds. Quantitative analyses of a series of the selected phosphinic acids with different enantiomeric purities show the high accuracy of this method.

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1,1′-[1,3-Phenylenebis[(S)-[[(1S)-1-(2-naphthyl)ethyl]amino]methylene]]bis-(2-naphthalenol)C52H44N2O2[α]D20=+280.0 (c 0.51, THF)Source of chirality: (S)-α-(2-naphthyl)-ethylamineAbsolute configuration: (S,S,S,S)

(12S,18S)-N12,N18-Bis[(1S)-1-(2-naphthyl)ethyl]-{2H,8H,12H,18H-13,17-metheno-3,7-nitrilo-dinaphtho[2,1-j:1′,2′-s][1,9]dioxacycloeicosin-12,18-diamine}C59H49N3O2[α]D20=+19.6 (c 0.23, THF)Source of chirality: (S)-α-(2-naphthyl)-ethylamineAbsolute configuration: (S,S,S,S)