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Brett A. Hopkins and Prof. Dr. John P. Wolfe Synthesis of Enantiomerically Enriched Imidazolidin-2-Ones through Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions Angewandte Chemie International Edition 51

Article first published online: 31 AUG 2012 | DOI: 10.1002/anie.201205233

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Positive water effect: A catalyst composed of [Pd2(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[BOND]C bond-forming reductive elimination is the enantiodetermining step in these reactions.

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