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Letter

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

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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

Org. Lett., 2006, 8 (12), pp 2531–2534

DOI: 10.1021/ol060707b

Publication Date (Web): May 16, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jpwolfe@umich.edu

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^tBu.

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Published In Issue June 08, 2006
Received March 22, 2006

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Letter

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

A Concise Asymmetric Synthesis of cis-2,6-Disubstituted N-Aryl Piperazines via Pd-Catalyzed Carboamination Reactions

Mild Conditions for the Synthesis of Functionalized Pyrrolidines via Pd-Catalyzed Carboamination Reactions

Selective Synthesis of 5- or 6-Aryl Octahydrocyclopenta[b]pyrroles from a Common Precursor through Control of Competing Pathways in a Pd-Catalyzed Reaction

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