Highly Enantioselective Desymmetrization of Meso Anhydrides by a Bifunctional Thiourea-Based Organocatalyst at Low Catalyst Loadings and Room Temperature

Bifunctional (thio)urea-based cinchona alkaloid derivatives have been shown to promote highly efficient enantioselective desymmetrization reactions of meso anhydrides. The most selective of these catalysts is capable of the enantioselective methanolysis of succinic and glutaric anhydride derivatives to form hemiester products with >90% yield and enantiomeric excess at 1 mol % loading and ambient temperature.