Enantioselective Diamination of Alkenes by Use of a Bisimidoosmium Reagent with the Aid of Chiral Catalysts

Abstract

Abstract 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)