Organic Chemistry Portal



A New Practical Method for the Osmium-Catalyzed Dihydroxylation of Olefins using Bleach as the Terminal Oxidant

Gerald M. Mehltretter, Santosh Bhor, Markus Klawonn, Christian Döbler, Uta Sundermeier, Markus Eckert, Hans-Christian Militzer, Matthias Beller*

*Institut für Organische Katalyseforschung (IfOK) an der Universität Rostock e.V., Buchbinderstr. 5-6, 18055 Rostock, Germany, Email:

G. M. Mehltretter, S. Bhor, M. Klawonn, C. Döbler, U. Sundermeier, M. Eckert, H.-C. Militzer, M. Beller, Synthesis, 2003, 295-301.

DOI: 10.1055/s-2003-36822


A general procedure for the osmium-catalyzed dihydroxylation of various terminal and internal olefins using bleach as cheap oxidant yields the corresponding cis-1,2-diols in the presence of dihydroquinine or dihydroquinidine derivatives (Sharpless ligands) with good to excellent chemo- and enantioselectivities under optimized pH conditions.

see article for more examples

Key Words

Sharpless dihydroxylation, sodium hypochlorite, asymmetric catalysis, homogenous catalysis, osmium, oxidations

ID: J66-Y2003-1760