The Disubstitution of Acetals to Prepare ,-Bis(aryl) -Keto Esters
Daniel L Priebbenow, Liang-Hua Zou, Peter Becker, Carsten Bolm
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | WILEY-V C H VERLAG GMBH | Published : 2013
An efficient catalytic protocol for the synthesis of δ,δ- bis(aryl)-substituted β-keto esters has been developed. This method involves the Lewis acid catalysed disubstitution reaction of ester-substituted silyl enol ether acetals with a series of aromatic nucleophiles to afford valuable functionalized β-keto esters with several sites available for further derivatisation. An efficient protocol for the conversion of silyl enol acetals into δ,δ-bis(aryl) β-keto esters was developed. In the presence of an aromatic nucleophile, activation of the acetal by a catalytic amount of Lewis acid facilitates the disubstitution reaction to afford a series of valuable functionalised β-keto esters. Copyright..View full abstract
In part, this research was supported by the Cluster of Excellence (Tailor-Made Fuels from Biomass) funded by the Excellence Initiative of the German Federal and State Governments. The authors acknowledge the Alexander von Humboldt Foundation for a post-doctoral fellowship to D. L. P. and the Chinese Scholarship Council (CSC) for a predoctoral stipend to L. H. Z.