Alcohol Cross-Coupling for the Kinetic Resolution of Diols via Oxidative Esterification

We present an organocatalytic C–O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, <i>m</i>-CPBA as the oxidant, and <i>N</i>,<i>N</i>′-diisopropyl­carbodi­imide as the activating agent. Racemic acyclic diols as well as <i>trans</i>-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols