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Synthesis 2012(4): 600-604  
DOI: 10.1055/s-0031-1289674
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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
Fax: +49(681)3022409; e-Mail: u.kazmaier@mx.uni-saarland.de;
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Publication History

Received 23 November 2011
Publication Date:
23 January 2012 (online)

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Abstract

Chelated enolates were found to be good nucleophiles for reactions with acyl halides 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 halides used. Besides acyl halides, also the corresponding imidazolides can be used with similar success. With chloroformates as acylating agents different protected amino malonates become accessible.

Key words

acylation - acyl halides - amino acids - amino malonates - chelated enolates - ketones

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