The determination of the enantiomeric excess and absolute configuration of chiral compounds is indispensable in synthetic, pharmaceutical, and biological chemistry. In this article, we describe an efficient 19 F nuclear magnetic resonance (NMR)based analytical protocol for determining the enantiomeric excess and absolute configuration of in situ fluorine-labeled amines and alcohols. 2-Fluorobenzoylation was used to convert analytes to fluorinated amides or esters. The resulting F-labeled analytes were mixed with a cationic cobalt(III) complex, [Co]BArF, resulting in clean baseline peak separations of analyte enantiomers in 19 F{ 1 H} NMR spectra. The measured Δδ RS signs were unambiguously used to correlate the absolute configurations of amines, amino alcohols, and alcohols. Moreover, the structure-dependent 19 F{ 1 H} NMR signals enabled absolute configuration determination by analyzing the relative chemical shifts of enantiopure analyte samples with [Co]BArF and ent-[Co]BArF.

Herein, efficient chiral recognition of phosphine oxides with octahedral indium complexes was demonstrated. Direct chiral analysis of in situ-prepared phosphine oxides formed using phosphines and hydrogen peroxide was conducted effectively via 31P nuclear magnetic resonance spectroscopy. Sufficient peak resolution of chiral phosphines was obtained consistently, thereby enabling the reliable determination of absolute chirality. Rational 1:1 binding models based on experiments and density functional theory calculations have been proposed.

Determining the chirality of phosphoric acids can be a challenging task. In this study, we present a novel approach for the chiral recognition of phosphates using cationic octahedral cobalt complexes. By utilizing 31P NMR spectroscopy, we are able to accurately measure the enantiopurities of chiral phosphoric acids after forming ion pairs with the cobalt complexes. We have successfully applied this method to a variety of chiral phosphoric acids derived from BINOL, H8-BINOL, SPINOL, VAPOL, and VANOL compounds, as well as ATP, and were able to efficiently resolve them in 31P­{1H} NMR spectra. Furthermore, we were able to achieve an optical resolution of a phosphoric acid with an enantiomeric excess of greater than 99%.

We present a novel approach utilizing 19F-nuclear magnetic resonance (NMR) spectroscopy for serum amine profiling. Our method introduces a highly efficient and reliable technique for fluorine labeling of amine metabolites via Schiff base formation. By employing this fluorine labeling, we successfully achieve accurate identification and quantification of amine metabolites in human serums, providing valuable insights for metabolomics research.