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Paper | Special issue | Vol 74, No. 1, 2007, pp.731-742
Published online, 26th October, 2007
DOI: 10.3987/COM-07-S(W)58
Synthesis of 4-Benzyliden-2-oxazolidinone Derivatives via Gold-Catalyzed Intramolecular Hydroamination

Stefanie Ritter, Kristina Hackelöer, and Hans-Günther Schmalz*

*Institute of Organic Chemistry, University of Kologne, Greinstr. 4, 50939 Köln, Germany

Abstract

AuCl-catalyzed intramolecular hydroamination of N-aryl-O-propargyl carbamates (3) efficiently affords (Z)-N-aryl-4-benzyliden-2-oxazolidinones (4) via a 5-exo dig cyclization. The reaction proceeds in acetonitrile at 60 °C and requires tBuOK or KOH as a base co-catalyst. It tolerates the presence of multiple substituted aryl units with electron donating methoxy groups. The method opens a convenient, flexible and operationally simple access to a new class of twisted molecules with potentially interesting biological properties.