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Enantioselective Diamination of Alkenes by Use of a Bisimidoosmium Reagent with the Aid of Chiral Catalysts
Author(s) -
Almodovar Iriux,
Hövelmann Claas H.,
Streuff Jan,
Nieger Martin,
Muñiz Kilian
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500641
Subject(s) - enantioselective synthesis , chemistry , catalysis , alkene , reagent , enantiomer , organic chemistry , stoichiometry , combinatorial chemistry
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)