Application of (S)-TBMB carboxylic acid-based on-line HPLC-exciton CD analysis to acyclic vicinal alcohols and amino alcohols

Abstract

Applications of the on-line HPLC-exciton CD analysis using (S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid [(S)-TBMBC-OH] that can simultaneously determine the enantiomeric compositions and the absolute configuration of cyclohexane-1,2-diols and diamines as well as acyclic vicinal diols and amino alcohols were studied. Di-O- or di-N,O-(S)-TBMBC derivatives of acyclic terminal vicinal diols, 2-hydroxy-1-amines, and nonterminal vicinal diols gave symmetrical exciton CD spectra between enantiomers, indicating their absolute configurations. However, Di-N,O-(S)-TBMBC derivatives of 2-amino-1-ols did not always give symmetrical exciton CD spectra between enantiomers, but their 2-phthalimido-1-O-(S)-TBMBC derivatives gave symmetrical exciton CD spectra, indicating their absolute configurations. All these (S)-TBMBC derivatives were separated by normal-phase HPLC and unequivocally determined by the on-line HPLC-exciton CD analysis without recourse to reference samples. Chirality 11:149–159, 1999. © 1999 Wiley-Liss, Inc.