Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid: A Chiral Derivatizing Agent for α-Chiral Primary Amines and Secondary Alcohols To Determine the Absolute Configuration

Autor: Kriegelstein, Michal, Profous, David, Lyčka, Antonín, Trávníček, Zdeněk, Přibylka, Adam, Volná, Tereza, Benická, Sandra, Cankař, Petr
Zdroj: The Journal of Organic Chemistry; September 2019, Vol. 84 Issue: 18 p11911-11921, 11p
Abstrakt: Racemic 2-(2-trifluoromethyl)-1H-benzo[d]imidazol-1-yl)benzoic acid (TBBA) was synthesized in three steps from 1-fluoro-2-nitrobenzene. Target (P)- and (M)-TBBA atropisomers were stable with a racemization barrier above 30 kcal/mol. As a chiral derivatizing agent, TBBA showed much higher differences in chemical shifts (ΔδPM) than the conventional Mosher’s acid.
Databáze: Supplemental Index