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DOI: 10.1055/sos-SD-036-00589

Nativi, C.; Roelens, S.Science of Synthesis, (200836757.

The catalytic dihydroxylation of alkenes represents a unique method for the synthesis of 1,2-diols with definite relative configuration. The syn-dihydroxylation of alkenes is often achieved using either osmium(VIII) oxide, potassium permanganate, or ruthenium(VIII) oxide as the catalyst; addition to the C=C bond occurs from the less hindered diastereotopic π-face. Due to the poor selectivity of potassium permanganate and ruthenium(VIII) oxidehydrogen peroxide systems, the syn-dihydroxylation of alkenes using osmium(VIII) oxide represents the most prominent method to obtain 1,2-diols from readily accessible starting materials.

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