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

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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