It was found that the oxirane ring is a functional group amenable to chiral discrimination by dirhodium-MTPA complexes. Considerable signal shifts up to 0.7 ppm are observed for 1 H nuclei close to the rhodium atoms in the complex. In analogy to previously reported olefins, this method appears to be
Application of NMR spectroscopy of chiral association complexes. 14—chiral recognition of terpene and cyclohexene hydrocarbons by 1H and 13C NMR
✍ Scribed by Werner Offermann; Albrecht Mannschreck
- Publisher
- John Wiley and Sons
- Year
- 1984
- Tongue
- English
- Weight
- 755 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Chiral NMR recognition of terpenic and similar hydrocarbons by Ag(fod) and optically active lanthanide shift reagents is descnloed. Twenty-four 'H signals of eight compounds and, as a first report in the literature, eleven I3C signals of three compounds were split into signal pairs due to the respective enantiomers. Although the magnitudes of the splittjngs are not connected to the structnre of the substrate molecules in an obviouS manner, the con6gwathns of the similar compounds camphene and epi-b-santalene were related empirically. AU spectra were sdiaently resolved to allow separate integration of enantiomer signals; from the integrals the enantiomeric purities of seven non-racemic mixtures were determined with good accuracy. The shift curves made several hitherto unknown assignments feasible.
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