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: osmo.hormioulu.fi

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

DOI: 10.1021/jo0496749

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Abstract

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.

see article for more examples

proposed mechanism

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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.

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Key Words

Sharpless Dihydroxylation, Sodium Chlorite

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ID: J42-Y2004-570