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Mild and High-Yielding Synthesis of β-Keto Esters and β-Ketoamides

Vellaisamy Sridharan, Miriam Ruiz, J. Carlos Menéndez*

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain, Email:

V. Sridharan, M. Ruiz, J. C. Menéndez, Synthesis, 2010, 1053-1057.

DOI: 10.1055/s-0029-1217135


In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols or primary or secondary amines could be carried out in refluxing tetrahydrofuran. Under these much milder conditions, side products were avoided, and β-keto esters and β-ketoamides were normally obtained in quantitative yields.

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Key Words

acetoacetylation, chiral auxiliaries, dicarbonyl compounds, esters, amides

ID: J66-Y2010-0790