Sodium chlorite as an efficient oxidant and hydroxy ion pump in osmium-catalyzed asymmetric dihydroxylation

Mikko H Junttila; Osmo E O Hormi

doi:10.1021/jo0496749

Sodium chlorite as an efficient oxidant and hydroxy ion pump in osmium-catalyzed asymmetric dihydroxylation

J Org Chem. 2004 Jul 9;69(14):4816-20. doi: 10.1021/jo0496749.

Authors

Mikko H Junttila¹, Osmo E O Hormi

Affiliation

¹ Department of Chemistry, University of Oulu, P O Box 3000, FIN-90014 Oulu, Finland.

PMID: 15230608
DOI: 10.1021/jo0496749

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 K(3)[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.