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36.7.1.1.1 Method 1: Dihydroxylation of Alkenes

DOI: 10.1055/sos-SD-036-00589

Nativi, C.; Roelens, S., Science of Synthesis, (2008) 36, 757.

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) oxide–hydrogen 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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References

[5] Meeeeeee, M. M., Mee. Meeee. Meee. Mee., (8888) 88, 8888.
[6] Meeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 88.
[7] Meeeee, M. M.; Meeeeeee, M., Mee. Meee. Mee., (8888) 88, 888.
[8] Meeee, M. M., M. Mee. Meee., (8888) 88, 888.
[9] Meeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee Meee., (8888), 8888.

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