= Asymmetric dihydroxylation
<Asymmetric dihydroxylation> adds two hydroxyl groups across an <alkene> while favouring one stereochemical product. In the Sharpless approach, a chiral ligand controls an osmium-based catalytic environment, turning an otherwise face-symmetric reaction into an enantioselective transformation.<Searching for New Reactivity by K. Barry Sharpless>[Account of ligand-controlled osmium-catalyzed asymmetric dihydroxylation]{ref}
The new <oxygen>-bearing centres are formed in a correlated addition. Substrate geometry and the ligand's handedness jointly determine which <stereoisomer> is favoured.
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