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Sodium Chlorite as an Efficient Oxidant and Hydroxy Ion Pump in Osmium-Catalyzed Asymmetric Dihydroxylation

Mikko H. Junttila and Osmo E. O. Hormi*

*Department of Chemistry, University of Oulu, P.O. Box 3000, FIN-90014 Oulu, Finland, Email:

M. H. Junttila, O. E. O. Hormi, J. Org. Chem., 2004, 69, 4816-4820.

DOI: 10.1021/jo0496749


Sodium chlorite is an efficient stoichiometric oxidant in Sharpless asymmetric dihydroxylation. The conversion of styrene was achieved twice as fast as in the established Sharpless K3[Fe(CN)6] dihydroxylation. Eight olefins were dihydroxylated to corresponding vicinal diols with yields and ees as good as those reported in the literature for other similar processes.

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proposed mechanism

Methanesulfonamide: a Cosolvent and a General Acid Catalyst in Sharpless Asymmetric Dihydroxylations

M. H. Junttila, O. O. E. Hormi, J. Org. Chem., 2009, 74, 3038-3047.

Key Words

Sharpless Dihydroxylation, Sodium Chlorite

ID: J42-Y2004-570