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. 2012 Sep 24;51(39):9886-90.
doi: 10.1002/anie.201205233. Epub 2012 Aug 31.

Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions

Brett A Hopkins  1 , John P Wolfe
Affiliations

Synthesis of enantiomerically enriched imidazolidin-2-ones through asymmetric palladium-catalyzed alkene carboamination reactions

Brett A Hopkins et al. Angew Chem Int Ed Engl. .

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.

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Figures

Scheme 1
Scheme 1
Stereochemistry of urea vs. pyrrolidine formation.
Scheme 2
Scheme 2
Mechanism of urea formation vs. pyrrolidine formation.
See this image and copyright information in PMC

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