Highly potent chiral labeling reagents for the discrimination of chiral alcohols.

Abstract

Highly sensitive chiral labeling reagents, (1R,2R)- and (1S,2S)-2-(2,3-anthracenedicarboximido)cyclohexanecarboxylic acids [(1R,2R)- and (1S,2S)-A] and (1R,2R)- and (1S,2S)-2-(2,3-naphthalenedicarboximido)cyclohexanecarboxylic acids [(1R,2R)- and (1S,2S)-A'], were prepared. Reagent A has enabled us to discriminate the enantiomers of anteiso fatty alcohols up to C9 methyl branching by 1H NMR, and both reagents A and A' have allowed up to C16 methyl branching at the 10(-15) molar level by fluorescence detected reversed-phase HPLC.