Synthesis and Evaluation of FICA Derivatives as Chiral Derivatizing Agents.

Autor: Kamei T; Faculty of Pharmaceutical Sciences, Josai International University., Takahashi T; Faculty of Pharmaceutical Sciences, Josai International University., Teramae H; Faculty of Science, Josai University., Koyanagi J; Faculty of Pharmaceutical Sciences, Josai International University.
Jazyk: angličtina
Zdroj: Chemical & pharmaceutical bulletin [Chem Pharm Bull (Tokyo)] 2020; Vol. 68 (8), pp. 818-821.
DOI: 10.1248/cpb.c20-00307
Abstrakt: 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 19 F- and 1 H-NMR spectroscopy. Introduction of a substituent at the 4-position in the benzene ring caused a 1.2-2 fold increase in Δδ F values when compared with that of FICA. This increase was investigated using a correlation model for 19 F-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.
Databáze: MEDLINE