The preparation, characterization and application of a new stationary phase derived from 1,4-cyclohexanedione and diethyl (+)-tartrate are described. A suitable TADDOL for immobilization has been synthesized and grafted to a γ-mercaptopropylsilylated silica gel. The resulting modified stationary phase has been characterized and its ability to separate enantiomers has been studied. While the free TADDOL in solution was able to resolve a range of enantiomers, the resolving properties were lost on immobilization. Solid state 13C CPMAS NMR of the new stationary phase was used to explain the lack of stereoselective recognition.
Legrand, S., Heikkinen, H., Nicholls, I. A., Root, A., Svenson, J., & Unelius, C. R. (2010). Preparation, characterization and application of a stationary chromatographic phase from a new (+)-tartaric acid derivative. Tetrahedron Letters, 51(17), 2258-2261. https://doi.org/10.1016/j.tetlet.2010.02.101