title: Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions.
abstract: Positive water effect: A catalyst composed of [Pd(2)(dba)(3)] (dba=dibenzylideneacetone) and (S)-Siphos-PE is effective for the enantioselective coupling of N-allyl ureas with aryl bromides to afford 4-substituted imidazolidin-2-ones. Added water leads to significantly improved enantioselectivities with electron-poor aryl halide substrates. It is suggested that the C-C bond-forming reductive elimination is the enantiodetermining step in these reactions.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USA.
authors.forename: Brett A
authors.initials: BA
authors.lastname: Hopkins
authors.forename: John P
authors.initials: JP
authors.lastname: Wolfe
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D048289:Imidazolidines; D010165:Palladium