Stereoisomeric flavour compounds. LXXVIII. Separation and structure elucidation of the pyranoid linalool oxide stereoisomers using common gas chromatographic phases, modified cyclodextrin phases and nuclear magnetic resonance spectroscopy
✍ Scribed by Barbara Weinert; Matthias Wüst; Armin MosandL; Helmut Hanssum
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 134 KB
- Volume
- 9
- Category
- Article
- ISSN
- 0958-0344
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✦ Synopsis
Using common non-chiral gas chromatographic phases and modified cyclodextrin phases, the direct stereodifferentiation of the four pyranoid linalool oxide stereoisomers has been achieved. The structure elucidation of the two geometrical isomers by 1 H nuclear magnetic resonance (NMR) spectroscopy (including intramolecular nuclear Overhauser effects of the separated diastereoisomers) and 13 C NMR spectroscopy is reported. The elution order of the optical isomers was ascertained by synthesis and chromatography of the (2R)configured diastereomers, starting from (R)-linalool.