Asymmetric reaction optimization has become a vital part across the chemical and pharmaceutical sciences. Unfortunately, determination of optimal reaction conditions is often time consuming and labor intensive. Chiroptical sensing has recently gained interest as a rapid technique for screening asymmetric reactions and important biomolecules. We have introduced an array of chirality sensors for this purpose. Some of these probes are designed to undergo covalent bond formation with a chiral target, which results in strong circular dichroism and UV-Vis signals that are used to determine the absolute configuration, enantiomeric excess and sample concentration of chiral compounds. The generality and practicality of this approach is demonstrated with the determination of the enantiomeric excess and the yield of asymmetric crude reaction mixtures. The chirality sensing is completed within a fraction of the time needed for traditional methods and requires minute amounts of crude materials. This strategy facilitates reaction scale miniaturization, adaption to high-throughput analysis equipment, i.e. multi-well plate CD/UV readers, while eliminating workup and chiral HPLC analysis, thereby reducing labor, time and waste production.

Accelerated asymmetric reaction screening and sensing of chiral compounds using small molecular probes

2019 Fall National Meeting

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