Dynamic Kinetic Resolution of Secondary Diols via Coupled Ruthenium and Enzyme Catalysis

Abstract

Enzymatic acylation of secondary symmetrical diols (as meso/dl mixtures) in combination with ruthenium-catalyzed isomerization of the diol led to efficient dynamic kinetic resolution. In this way, a meso/dl mixture of the diol was transformed to enantiomerically pure (R,R)-diacetate, making efficient use of all the diol material. For some of the flexible substrates, substantial amounts of meso-diacetates were formed as side products. The results indicate that the major part of the meso product is formed via an intramolecular acyl-transfer pathway.