SPECIALTOPIC	Synthesis 2006: 3341-3347   DOI: 10.1055/s-2006-950228
© Georg Thieme Verlag Stuttgart · New York
Aromatic Nitro Groups and Their Reactions with Chelated Ester Enolates
Daniel Stolz, Uli Kazmaier*, Rigobert Pick
Institut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany Fax: +49(681)3022409; e-Mail: u.kazmaier@mx.uni-saarland.de;
Received 1 May 2006

Abstract

Chelated amino acid ester enolates react with aromatic nitro compounds in a 1,3-addition mode at the nitro group giving amino acids bearing an aryl(hydroxy)amino side chain. Best results were obtained with trifluoroacetyl-protected glycinates. Two equivalents of enolate are necessary for complete conversion, because one equivalent is oxidized during the reaction.

Key words

amino acids - chelates - enolates - nitroarenes - nitrosoarenes