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