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Synthesis of 2-Oxazolones and α-Aminoketones via Palladium-Catalyzed Reaction of β,β-Dibromoenamides

David I. Chai, Laura Hoffmeister and Mark Lautens*

*Davenport Research Laboratory, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6, Email: mlautenschem.utoronto.ca

D. I. Chai, L. Hoffmeister, M. Lautens, Org. Lett., 2011, 13, 106-109.

DOI: 10.1021/ol102634c (free Supporting Information)


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Abstract

General and efficient methods allow the synthesis of 2-oxazolones and α-aminoketones from β,β-dibromoenamides depending on the choice of R groups and the reaction conditions. On the basis of mechanistic studies, both reactions proceed via an intermolecular Suzuki-Miyaura C-C coupling and an intramolecular C-O coupling.

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Key Words

2-oxazolones


ID: J54-Y2011-0040