The alcohol functional group is widely found in natural products such as terpenes, steroids and saccharides. Alcohols are valuable building blocks for the synthesis of complex pharmaceuticals. Hence the development of protocols for enantiomeric excess (ee) analysis of alcohols is of great interest. Furthermore, high-throughput ee screening (HTS) has become crucial due to advances in methods of parallel synthesis and combinatorial synthesis. Parallel synthesis uses equipment and facilities such as microwell plates, microreactors and miniblock reactors. This equipment enables one to optimize experimental conditions by changing solvent, pH, catalyst etc in parallel. Here, we present a procedure for the parallel synthesis of homo-allylic alcohols in combination with a HTS method involving a dynamic covalent multi-component assembly for chirality sensing.The ee screening method uses a reversible tetradentate ligand-based assembly that incorporates the chiral alcohols. The incorporation of alcohols into the ligand structure induces a twist which causes large Cotton effects in the circular dichroism (CD) spectra, which are indicative of the handedness of the alcohol. Based on the CD data, calibration curves were generated to predict ee for secondary and homo-allylic alcohols.

Determination of enantiomeric excess of chiral alcohols using a dynamic multi-component assembly

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.