Cyclodextrins as NMR probes in the study of the enantiomeric compositions of N-benzyloxycarbonylamino-phosphonic and phosphinic acids

Organophosphorus Supramolecular Chemistry Part 1. Receptors for Organophosphorus Compounds

“…This ability is used in the most efficient way in analytical chemistry where CDs play role as chiral selectors in discrimination of enantiomers of wide range of organic compounds. Thus, -and -CDs were successfully applied for determination of optical purity of a series of aminophosphonic and aminophosphinic acids and their derivatives by means of capillary [109,110]. The same type of CDs was also applied to analyze of enantiomeric composition of 1,1'-binaphtyl-2,2'-diylhydrogen phosphate by means of chiral fluorescence anisotropy [111].…”

“…On the basis of the Job plots, 2D-ROESY NMR experiments and molecular modeling it was shown that in the case of N-benzyloxycarbonyl derivative of phosphonic analogue of leucine all three types of complexes might exist simultaneously in solution in a dynamic equilibrium (Fig. (11)) [110].…”

“…It was shown that, heptakis(2,6-O-dimethyl)--CD [108], heptakis(2,6-O-dimethyl)--CD [107] as well as another derivatives of CDs such as acetylated--CD [129] and hydroxypropyl analogues of -, -and -CDs [107,108,110] create stereospecifically inclusion complexes with structurally variable aminophosphonates. Thus, they were successfully applied as chiral additives in high performance liquid chromatography [129], capillary electrophoresis [107,108] and NMR spectroscopy [110] for enantiodiscrimination of aminophosphonic and aminophosphinic acids and their derivatives.…”

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

“…17,18 Some chiral amines, such as a-phenylethylamine, 19 a-(1-naphthyl)-ethylamine, 19,20 and ephedrine, 19,20 have been used as CSAs for a-aminophosphonic and a-hydroxylphosphonic acids, but the peaks are not often baseline separated, because their chemical shift differences are generally too small. Some better examples [21][22][23] have been reported by Kafarshi and co-workers, employing cyclodextrins as CSAs for a-aminophosphonic and a-aminophosphinic acids.…”

Chiral Separation of Novel α ‐Aminophosphonates Containing a Benzothiazole Moiety by Liquid Chromatography Using an Amylose Stationary Phase

“…[7][8][9] Among all methods, methods, chiral stationary phase (CSP) exhibits the most universal chiral recognition ability for enantioseparations in high performance liquid chromatography. [10][11][12][13][14][15] In our previous work, a series of α-aminophosphonates containing a benzothiazole moiety were designed and synthesized.…”