Highly enantioselective dihydroxylation of olefins by osmium tetroxide with chiral diamines

Article abstract of DOI:10.1016/S0040-4020(01)80234-9

Enantioselective dihydroxylation of olefins by osmium tetroxide with chiral diamines was examined. The hydroxylation employing 1 gave exceptionally high optical yields in the production of diols from mono-, trans-di-, and trisubstituted olefins. Virtually complete asymmetric induction was observed in the reaction of trans-β-methylstyrene. The stereochemical outcome of the asymmetric reaction strongly suggested that the oxidation proceeded via organometallacycle 14.