Asymmetric dihydroxylation of C,C double bonds using catalytic amounts
of osmium tetroxide, selenides, and air*
Alain Krief1, and Catherine Colaux-Castillo1,2
1Laboratoire de Chimie Organique de Synthèse,
Department of Chemistry, Facultés Universitaires Notre-Dame de
la Paix, 61 rue de Bruxelles, B-5000 Namur, Belgium; 2Fonds pour la
Formation à la Recherche dans l'Industrie et dans l'Agriculture,
5 Rue d'Egmont, B-1000, Bruxelles, B-1050, Belgium
Abstract: Selenides, selenoxides, osmium tetroxide, and potassium
osmate dihydrate are in equilibrium in aqueous tert-butanol containing
potassium carbonate. We took advantage of this feature to withdraw the
equilibrium in each of the two directions to produce allylalcohols from
allylselenides and diols from olefins. The latter reaction performed
in the presence of catalytic amounts of Cinchona alkaloids and osmium
tetroxide allows the enantioselective dihydroxylation of C,C double
bonds.
*Lecture presented at the 11th IUPAC International
Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
(OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are
presented in this issue, pp.1-186.
**Corresponding author.
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