Divergent Dynamic Kinetic Resolution of a Racemic Mixture of Four Stereoisomers via N-Heterocyclic Carbene Organocatalysis

Abstract

Racemic mixtures of four stereoisomers are easily formed via many fundamental organic transformations, but the direct utilities of these mixtures have been less studied and remain large challenges to date. In this work, we introduce a new method, i.e., divergent dynamic kinetic resolution, to achieve the separation of racemic mixtures of four stereoisomers. The hypothesis was proved by using a N-heterocyclic carbene-catalyzed benzoin reaction, which afforded two separable diastereomeric products bearing three consecutive stereocenters with good to excellent enantioselectivties. We believe that this resolution protocol will find applications in more transformations.

Keywords: benzoin; divergent dynamic kinetic resolution; organocatalysis; stereocenters; stereoisomers; tetralone.