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Synfacts 2009(7): 0776-0776  
DOI: 10.1055/s-0029-1217253
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Au-Promoted Conversion of Propargylic Benzoates into 1-Acyloxyvinyl Ketones

Contributor(s): Paul Knochel, Andrei Gavryushin
Y. Peng, L. Cui, G. Zhang, L. Zhang*
University of Nevada, Reno, USA
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Publikationsdatum:
22. Juni 2009 (online)

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Significance

This publication describes the first example of the gold-catalyzed oxidative C-O bond formation. The proposed mechanism includes a unique intramolecular migration of a ­carboxyl group. This method allows an efficient access to α-acyloxysubstituted enones, otherwise difficult to prepare, from readily available propargylic esters.