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Article

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

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

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

J. Org. Chem., 2004, 69 (14), pp 4816–4820

DOI: 10.1021/jo0496749

Publication Date (Web): June 15, 2004

To whom correspondece should be addressed. Phone: (+358) 8 553 1631. Fax: (+358) 8 553 1593.

, osmo.hormi@oulu.fi

Abstract

Sodium chlorite is an efficient stoichiometric oxidant in Sharpless asymmetric dihydroxylation. One sodium chlorite provides the reaction with the stoichiometric number of electrons and hydroxide ions needed to dihydroxylate two olefins without the consumption of any additional base. 100% conversion in sodium chlorite asymmetric dihydroxylation of styrene was achieved twice as fast as in the established Sharpless K₃[Fe(CN)₆] dihydroxylation. Even internal olefins were dihydroxylated fast with sodium chlorite without hydrolysis aids. 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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Published In Issue July 09, 2004
Received February 26, 2004

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Article

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