Dihydroxylation of alkenes is a powerful synthetic method with the asymmetric Sharpless dihydroxylation representing a prominent example. The practicality of the method is only hampered by the use of osmium and reduced effectiveness with cis-alkenes. Significant attention has been given to developing dihydroxylations which use less toxic metals or are completely free of a metal. Notwithstanding the previously reported achievements in this field, which are significant, we developed an efficient dihydroxylation method that is performed in water using N-bromosuccinimide. Our method involves three distinct steps of bromohydrin formation followed by epoxidation and then acid catalyzed hydrolysis to afford the desired diol. All three steps are performed in the same reaction flask and all three use water as a solvent. The method was originally developed with methyl cinnamate and was extended to a variety of alkenes. It is not a stereo or diastereoselective synthesis, but the two diastereomers can be separated by chromatography allowing for ready access to both syn and anti-diols.

Metal-free dihydroxylation of alkenes in water

ACS Spring 2022

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