The Assignment of the Absolute Configuration of β-Chiral Primary Alcohols with Axially Chiral Trifluoromethylbenzimidazolylbenzoic Acid
Michal Kriegelstein, David Profous, Adam Přibylka, Petr Cankař
Abstract
Axially chiral trifluoromethylbenzimidazolylbenzoic acid (TBBA) was used as a chiral derivatization agent for the assignment of the absolute configuration of β-chiral primary alcohols. The structures varied from simple aliphatic alcohols to complex cyclic systems and highly substituted sugar derivatives. The NMR-based method was successfully implemented to evaluate 17 compounds and displayed ΔδPM values higher than 0.1 ppm in most cases, which makes TBBA superior to MTPA and MPA and comparable to 9-AMA.
Topics & Concepts
ChemistryAbsolute configurationDerivatizationAxial symmetryChiral derivatizing agentPrimary (astronomy)Chiral auxiliaryOrganic chemistryCombinatorial chemistryStereochemistryChiral column chromatographyEnantioselective synthesisEnantiomerCatalysisHigh-performance liquid chromatographyEngineeringPhysicsAstronomyStructural engineeringMolecular spectroscopy and chiralityAxial and Atropisomeric Chirality SynthesisAnalytical Chemistry and Chromatography