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Synthesis 2010(6): 1053-1057  
DOI: 10.1055/s-0029-1217135
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© Georg Thieme Verlag Stuttgart ˙ New York

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
Fax: +34(91)3941822; e-Mail: josecm@farm.ucm.es;
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Publication History

Received 30 June 2009
Publication Date:
20 November 2009 (online)

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Abstract

In the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and β-keto esters and β-ketoamides were normally obtained in quantitative yields.

Key words

acetoacetylation - chiral auxiliaries - dicarbonyl compounds - esters - amides

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