Desymmetrization of meso-Diols via Covalent Substrate Binding Catalysis

Significance

The desymmetrization of meso-diols is a highly useful asymmetric transformation since it can provide synthetically valuable intermediates with theoretically quantitative yields. The authors utilized catalysts 1 as a substrate-binding module as well as a silyl chloride activator. High enantioselectivity was obtained for cyclic and acyclic meso-diols (er up to 97.5:2.5). Also, the substituent adjacent to the imidazole group affects the enantioselectivity dramatically and displays strong match/mismatch effects on the enantioselectivity.