The significance of chiral compounds in the life and material sciences demands development of enantioselective synthetic and analytical methods at a fast pace. Despite the general progress with high-throughput experimentation, the analysis of the enantiomeric composition and yield of asymmetric reaction products is usually tedious and time-consuming. In this regard, chiroptical methods have considerable promise. Herein we present a supramolecular chemosensor design that combines covalent substrate binding with a pronounced chirality amplification process. Circular dichroism (CD) analysis allows determination of the enantiomeric excess and absolute configuration of the chiral analyte while the amount of the target can be obtained by measuring a characteristic UV-VIS change. This chiroptical assay was successfully used for the determination of the ee, absolute configuration and yield of an amine produced by Ir-catalyzed asymmetric hydrogenation of an iminium salt. In comparison to traditional techniques, this robust mix-and-measure sensing protocol eliminates reaction workup, reduces analysis time and decreases chemical waste.

Sensing of chiral compounds via self-assembly with a stereodynamic probe

253rd National Meeting (2017)

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