Asymmetric dihydroxylation of C,C double bonds using catalytic amounts of osmium tetroxide, selenides, and air

Krief, Alain; Colaux-Castillo, Catherine

doi:10.1351/pac200274010107

Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 107-113

http://dx.doi.org/10.1351/pac200274010107

Asymmetric dihydroxylation of C,C double bonds using catalytic amounts of osmium tetroxide, selenides, and air

Alain Krief¹ and Catherine Colaux-Castillo^1,2

¹ Laboratoire de Chimie Organique de Synthèse, Department of Chemistry, Facultés Universitaires Notre-Dame de la Paix, 61 rue de Bruxelles, B-5000 Namur, Belgium
² Fonds 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.