Abstract
Axially dissymmetric 2′-methyl- and 2′-methoxy-1,1′-binaphthyl-2-carboxylic acid (1,2) were effectively utilized as chiral derivatizing agents for discrimination of enantiomeric alcohols and amines by high performance liquid chromatography (HPLC) on silica gel. Especially, 2 had excellent chirality-recognizing ability, and could also be utilized for discrimination by 1H NMR with the aid of Eu(fod)3. The elution behavior of a pair of diastereomeric esters or amides on HPLC, as well as the NMR behavior of the diastereomers were rationally explained based on X-ray crystallography analyses. Carbonyl cyanide derivatives of 1 and 2 were successfully applicable to resolution of β-adrenergic blocker enantiomers in biological fluids by HPLC. These diastereomeric esters were highly responsive to a fluorescence detector, the limit of detection being 200 pg and 30 pg (at a signal-to-noise ratio of 5), respectively. Also reported are convenient methods for the preparation of these reagents.
| Original language | English |
|---|---|
| Pages (from-to) | 986-996 |
| Number of pages | 11 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 50 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 1992 |
| Externally published | Yes |
Keywords
- 2′-Methoxy-1,1′-binaphthyl-2-carboxylic acid
- 2′-Methyl-1,1′-binaphthyl-2-carboxylic acid
- Chiral derivatizing agent
- Enantiomeric alcohol
- Enantiomeric amine
- Fluorescence detection
- H NMR
- High performance liquid chromatography
- β-Adrenergic blocker
ASJC Scopus subject areas
- Organic Chemistry