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A Straightforward Approach towards α-Amino-β-keto Esters via Acylation of Chelated Amino Acid Ester Enolates

Katharina Schultz, Laura Stief, Uli Kazmaier*

*Institut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany, Email:

K. Schultz, L. Stief, U. Kazmaier, Synthesis, 2012, 44, 600-604.

DOI: 10.1055/s-0031-1289674

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Chelated enolates are good nucleophiles for reactions with acyl halides and imidazolides affording α-amino-β-keto esters. In most cases, the reactions are over after a few minutes and preparatively useful yields are obtained, independent of the protecting groups and electrophile used. With chloroformates as acylating agents, protected amino malonates become accessible.

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Key Words

acylation (of esters, of amines), acyl halides, amino acids, amino malonates, chelated enolates, ketones

ID: J66-Y2012-0410