Method for the asymmetric dihydroxylation of olefins, using osmium catalysts

A process for the asymmetric dihydroxylation of olefins using osmium catalysts to prepare monofunctional, bifunctional and/or polyfunctional chiral 1,2-diols of the formula (I)

• R1R2C(OH)—C(OH)R3R4 (I)
• where
• R1 to R4 are each, independently of one another, hydrogen, alkyl, CN, COOH, COO-alkyl, COO-aryl, CO-alkyl, CO-aryl, O-alkyl, O-aryl, O—CO-aryl, O—CO-alkyl, OCOO-alkyl, N-alkyl2, NH-alkyl, N-aryl2, NH-aryl, NO, NO2, NOH, aryl, fluorine, chlorine, bromine, iodine, Si-alkyl3, CHO, SO3H, SO3-alkyl, SO2-alkyl, SO-alkyl, CF3, NHCO-alkyl, CONH2, CONH-alkyl, NHCOH, NHCOO-alkyl, CHCHCO2-alkyl, CHCHCO2H, PO-(aryl)2, PO(alkyl)2, PO3H2, or PO(O-alkyl)2, where alkyl is a linear, branched, and/or cyclic aliphatic organic group having from 1 to 18 carbon atoms and aryl is a five-, six-, or seven-membered aromatic ring containing from 4 to 14 carbon atoms and from 0 to 3 heteroatoms and is optionally fused, and where the alkyl and/or the aryl group optionally bears up to six substituents selected independently from the group consisting of hydrogen, alkyl, O-alkyl, OCO-alkyl, O-aryl, aryl, fluorine, chlorine, bromine, iodine, OH, NO2, NO, Si-alkyl3, CN, COOH, CHO, SO3H, NH2, NH-alkyl, N-alkyl2, PO-alkyl2, SO2-alkyl, SO-alkyl, CF3, NHCO-alkyl, COO-alkyl, CONH2, CO-alkyl, NHCOH, NHCOO-alkyl, CO-aryl, COO-aryl, PO-aryl2, PO3H2, PO(O-alkyl)2, and SO3-alkyl, where alkyl and aryl are as defined above,
• comprising reacting an olefin of the formula (II)
• R1R2C═CR3R4 (II)
• where R1 to R4 are defined as for formula (I),
• with molecular oxygen in the presence of an osmium compound and a chiral amine ligand in water or a water-containing solvent mixture at a pH of from 8.5 to 13.