Enantioselective diamination of alkenes by use of a bisimidoosmium reagent with the aid of chiral catalysts

The development of a new method for the diamination of alkenes is reported. It is based on a reaction in the presence of stoichiometric or catalytic amounts of chiral auxiliaries, which permits the direct synthesis of enantiomerically enriched osmaimidazolidines. The combined application of a catalyst-directing oxazolidinone group and a titanium catalyst results in enantioselective alkene diamination with enantiomer ratios of up to 95:5. Absolute configurations of representative osmaimidazolidine products were established unambiguously by solid-state structure analyses. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).