Sharpless Dihydroxylation

Abstract

This reaction is a transformation of olefins into syn ‐diols via an asymmetric cis ‐dihydroxylation in the presence of a catalytic amount of potassium osmate dihydrate using K 3 Fe(CN) 6 or NMO as an oxidant and is generally referred to as the Sharpless asymmetric dihydroxylation or Sharpless dihydroxylation. Generally, two reaction systems have been developed for the asymmetric transformation of olefins into syn ‐diols. The study finds that the reaction is especially suitable for the transformation of electron‐rich and sterically less hindered olefins. The Sharpless dihydroxylaton requires an enantiomerically pure molecule to induce the chirality, and many natural chiral molecules (e.g., alkaloids) are suitable for this purpose. Besides the dihydroxylation of olefins, the Sharpless asymmetric dihydroxylation has also been successfully used for the introduction of an α‐hydroxyl group adjacent to the carbonyl functionality, by means of the dihydroxylation of an enol ether. This reaction has a broad application in organic synthesis with respect to the preparation of molecules with syn ‐diol moieties.