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Synthesis of Enantiomerically Enriched Imidazolidin-2-Ones through Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions

Authors

  • Brett A. Hopkins,

    1. Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109-1055 (USA)
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  • Prof. Dr. John P. Wolfe

    Corresponding author
    1. Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109-1055 (USA)
    • Department of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109-1055 (USA)
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  • The authors acknowledge the NIH-NIGMS (GM 098314) for financial support of this work. Additional funding was provided by GlaxoSmithKline and Amgen. The authors thank Dr. Duy N. Mai for conducting preliminary experiments.

Abstract

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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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