A New Synthesis of Imidazolidin-2-ones via Pd-Catalyzed Carboamination of N-Allylureas

Jonathan A. Fritz, Josephine S. Nakhla and John P. Wolfe*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, Email: jpwolfeumich.edu

J. A. Fritz, J. S. Nakhla, J. P. Wolfe, Org. Lett., 2006, 8, 2531-2534.

DOI: 10.1021/ol060707b

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Abstract

Imidazolidin-2-ones are prepared in two steps from readily available N-allylamines. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-ones with generation of two bonds and up to two stereocenters in the presence of aryl bromides, a catalytic amount of Pd₂(dba)₃/Xantphos and NaOtBu.

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Key Words

Ureas, Imidazolidinones

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ID: J54-Y2006-1780