Transforming Racemic Compounds into Two New Enantioenriched Chiral Products via Intermediate Kinetic Resolution

Converting racemic compounds to enantioenriched products is an important and economic approach for accessing enantioenriched chiral molecules. A common method is kinetic resolution. Herein, we present a mode of kinetic resolution that transforms racemic compounds into enantioenriched products, in which the kinetic resolution of reaction intermediates is the key. Catalyzed by a single Ru complex, racemic allylic alcohols are shown to react with a glycine-derived Schiff base to afford two chiral compounds, a δ-carbonyl product and a δ-hydroxy variant, with good yields and stereoselectivities (up to >20:1 dr, 99% ee, 920 s factor). Mechanistic studies suggest that multiple hydrogen transfer events exist in the reaction: a dehydrogenative coupling process, which leads to a pair of racemic intermediates, and a transfer hydrogenation-enabled kinetic resolution process that resolves the intermediates, alongside H2 release at the catalyst.