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

Synthesis and applications of exo N-((1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)benzamides as NMR solvating agents for the chiral discrimination of 1,1′-binaphthyl-2,2′-diyl hydrogenphosphates and α-substituted acids

“…14 There are a few reports on the development and use of some chiral solvating agents to determine the composition of isomers of 5, an important catalyst by 31 P NMR analysis. 18 Although Kagan's amide 1a has been used as a probe to resolve the signals of compounds containing phosphorus by 31 P NMR, 10c,12a there are no reports on its use for the analysis of 5. The present set of chiral solvating agents, 4a-4h, was systematically screened to determine their efficiency to discriminate between the isomers of 5 by recording the separation of signals by the 31 P NMR analysis.…”

P–C bond formation via P–H addition of a fluoroaryl phosphinic acid to ketones

“…For a non-fluorinated α-hydroxy phosphinic acid obtained by the latter route the isolation and characterization with X-ray diffraction of a single enantiomer (S) could be achieved [20] . Applications of this class of compounds range from flame retardants [21] to asymmetric synthesis [22] and neutral amino peptidase (NAPN) inhibitors [23] .…”

Enantiodifferentiation of α‐hydroxyalkanephosphonic acids in 31P NMR with application of α‐cyclodextrin as chiral discriminating agent

“…46 Two chiral, camphane based macrocycles were reported to be useful in determination of the enantiomeric ratio of four ethyl hydroxyphenylmethanephosphinates by means of 1 H NMR. 50 According to our best knowledge only one report describes the direct analysis of free hydroksyphosphonic acids. 1-(1-Naphtyl)ethylamine was applied as CSA in that case.…”