Synthesis and Evaluation of FICA Derivatives as Chiral Derivatizing Agents.

ABSTRACT

1-Fluoroindan-1-carboxyic acid (FICA) derivatives containing a monosubstituted benzene ring (1b-e) were synthesized as their methyl esters and their potential as chiral derivatizing agents (CDAs) were assessed by both 19F- and 1H-NMR spectroscopy. Introduction of a substituent at the 4-position in the benzene ring caused a 1.2-2 fold increase in ΔδF values when compared with that of FICA. This increase was investigated using a correlation model for 19F-NMR and by the order of the stability of the synperiplanar (sp) and antiperiplanar (ap) conformers of the (R,S) and (S,S) diastereomers from the Gibbs' free energy at 298.15 K.