Reengineering a Reversible Covalent-Bonding Assembly to Optically Detect ee in β-Chiral Primary Alcohols

Summary The use of parallel synthesis protocols for asymmetric reaction discovery has increased the need for new methods to rapidly determine enantiomeric excess (ee) values. Most chirality sensing is performed on stereocenters that are α (i.e., proximal) to the target functional group. Finding a general approach to detect more distant point chirality would increase the substrate scope of such assays. Herein, we demonstrate a design principle to “reach out” to more distant stereocenters, in this case β-chirality in primary alcohols. Therefore, we see the design principles established in this work as a step forward in sensing distant point chirality and, eventually, multi-stereocenter relationships.