A Highly Efficient Preparative Method of α-Ylidene-β-Diketones via AuIII-Catalyzed Acyl Migration of Propargylic Esters
- 9 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (26), 8414-8415
- https://doi.org/10.1021/ja062777j
Abstract
A highly efficient synthesis of alpha-alkylidene or benzylidene-beta-diketones from readily available propargylic esters has been developed. The proposed key transformation is a novel intramolecular acyl migration to nucleophilic AuIII-C(sp2) bonds. Noteworthy features of this method are its efficiency and stereoselectivity. The yields of this reaction were mostly close to quantitative, and high to excellent stereoselectivities were observed in the cases of dienyl beta-diketones.Keywords
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