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.
Synthesis of Enantiomerically Enriched Imidazolidin-2-Ones through Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions†
Article first published online: 31 AUG 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 39, pages 9886–9890, September 24, 2012
How to Cite
Hopkins, B. A. and Wolfe, J. P. (2012), Synthesis of Enantiomerically Enriched Imidazolidin-2-Ones through Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions . Angew. Chem. Int. Ed., 51: 9886–9890. doi: 10.1002/anie.201205233
- Issue published online: 19 SEP 2012
- Article first published online: 31 AUG 2012
- Manuscript Received: 3 JUL 2012
- asymmetric catalysis;
- asymmetric synthesis;
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 CC bond-forming reductive elimination is the enantiodetermining step in these reactions.