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Synfacts 2006(10): 1036-1036
DOI: 10.1055/s-2006-949275
DOI: 10.1055/s-2006-949275
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Au(III)-Catalyzed Stereoselective Synthesis of Alkylidene β-Diketones
S. Wang, L. Zhang*
University of Nevada, Reno, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. September 2006 (online)
Significance
A variety of propargyl esters were efficiently converted into alkylidene β-diketones in the presence of a Au(III)/pyridine-2-carboxylate catalyst. Excellent yields were reported, as well as short reaction times (<1 day, but generally 0.4-5 h). E/Z ratios of the products were fair to good when propargyl acetates or benzoates were used, but were excellent with propargyl acrylates or carbamates. Mechanistic studies support the formation of an intermediate allenyl ester, as they are converted into the products under the reaction conditions.