Asymmetric Dihydroxylation of olefins is of high synthetic value because it introduces two vicinal hydroxy groups, endowing prochiral olefinic carbon(s) with chirality. Some oxo metal species of high valency, such as permanganate, ruthenium tetroxide, and osmium tetroxide undergo stereospecific cis-dihydroxylation. Among them, the osmium-mediated dihydroxylation is highly chemoselective and can be applied to a wide range of olefins. Thus, osmium-mediated asymmetric dihydroxylation has been extensively studied.

Sharpless and co-workers reported that dihydroxylation was catalytically effected, with good enantioselectivity and remarkable ligand acceleration, when Cinchona Alkaloid ligands based on DHQD or DHQ was used as the chiral auxiliary.