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Synfacts 2006(10): 1002-1002  
DOI: 10.1055/s-2006-949352
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Carboaminative Route to Imidazolidin-2-ones

Contributor(s): Victor Snieckus, Heiko Scharl
J. A. Fritz, J. S. Nakhla, J. P. Wolfe*
University of Michigan, Ann Arbor, USA
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

An innovative synthetic strategy for imidazolidinones (cyclic ureas) involving Pd-catalyzed carboamination is described. Although a broad range of yields is reported, the reaction sequence is conveniently carried out starting from readily available allylic amines and proceeds with excellent diastereoselectivity. Imidazolidinones are significant bioactive structural units, for example, in molecules with potent anti-HIV activity (W. M. Kazmierski et al. Bioorg. Med. Chem. Lett. 2004, 14, 5685-5687).