<i>N</i>-Heterocyclic-carbene-catalyzed <i>meso</i>-1,2-diol asymmetric desymmetrization

Abstract Chiral building blocks containing two continuous hydroxy groups are valuable compounds that are hard to produce enantioselectively in high yields. Herein, we report the N-heterocyclic-carbene-catalyzed (NHC-catalyzed) desymmetrizations of meso-1,2-diols using α-benzoyloxy aldehydes that afford mono-acylated diols with moderate-to-high enantioselectivities and chemical yields. Our original pyridine-bearing NHC plays an important role in delivering good enantioselectivity. This reaction was successfully applied to a wide range of meso-1,2-diols.