Organic Letters 2006-06-08

A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas.

Jonathan A Fritz, Josephine S Nakhla, John P Wolfe

Index: Org. Lett. 8(12) , 2531-4, (2006)

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Abstract

A new strategy for the preparation of substituted imidazolidin-2-ones in two steps from readily available N-allylamines is described. Addition of the amine starting materials to isocyanates affords N-allylureas, which are converted to imidazolidin-2-one products with generation of two bonds and up to two stereocenters when treated with aryl bromides and catalytic amounts of Pd2(dba)3/Xantphos in the presence of NaO(t)Bu. [reaction: see text]