(S)-Tetrahydro-5-oxo-2-furancarboxylic Acid: A Chiral Derivatizing Reagent for Asymmetric Alcohols

Article abstract of DOI:10.1021/jo00200a003

The use of (S)-tetrahydro-5-oxo-2-furancarboxylic (TOF) acid as a potential derivatizing reagent for the determination of the enantiomeric composition of chiral alcohols was investigated.A series of chiral alcohols of widely varying structural type were derivatized with this acid and compared with two widely used acids (S)-α-acetoxypropanoic and (S)-α-methoxy-α-(trifluormethyl)phenylacetic.The resolution of the diastereomeric esters was measured on five different cappillary gas chromatographic (CGC) columns and one high-performance liquid chromatographic (HPLC) column.The 13C NMR spectra of these derivatives were recorded and examined for possible correlations between configuration and carbon chemical shift values.The chromatographic data provide a starting point for the selection of a derivatizing agent and column combination applicable to the CGC analysis of chiral alcohol enantiomeric purity, and the HPLC data allow selection of a derivatizing agent and solvent system for the HPLC analytical or preparative resolution of a chiral alcohol.The 13C NMR data provide information applicable to the assignment of the configuration to the resolved diastereomers.