Application of (S)-TBMB carboxylic acid-based on-line HPLC-exciton CD analysis to acyclic vicinal alcohols and amino alcohols
✍ Scribed by Kumi Shimizu; Jeong-Hwan Kim; Kazuaki Akasaka; Hiroshi Ohrui
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 448 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0899-0042
No coin nor oath required. For personal study only.
✦ Synopsis
Applications of the on-line HPLC-exciton CD analysis using (S)-2-tertbutyl-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.