Absolute Configuration Determination of Amines Using Kinetic Resolution Reagents

Despite recent advances in enantioselective transformations, the assignment of absolute configuration to natural products and synthetic intermediates remains a challenge. Several methods have been developed to determine the absolute configuration of molecules including the circular dichroism exciton method, Kishi’s NMR database, Horeau’s method, and Mosher NMR analysis.

The Mosher analysis is the most common technique, however it is a time consuming and difficult process. This report will describe a new strategy for determining the absolute configuration of primary and secondary amines using kinetic resolution reagents. Like kinetic resolution, this method relies on the difference in reaction rates between an enantioenriched amine and enantiomers of a chiral reagent. Further details on the development and scope of this new technique will be presented.