Synthesis 2006(16): 2719-2724  
DOI: 10.1055/s-2006-942497
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Oxo-2,3-dihydropyrrole Amino Acids as Chiral Dipeptidomimics

Prantik Maity, Burkhard König*
Institut für Organische Chemie, Universität Regensburg, 93040 Regensburg, Germany
Fax: +49(941)9431717; e-Mail: Burkhard.koenig@chemie.uni-regensburg.de;
Further Information

Publication History

Received 20 April 2006
Publication Date:
19 July 2006 (eFirst)

Abstract

We describe the synthesis of a novel chiral dipeptide β-sheet mimic based on aminomethyl-3-oxo-2,3-dihydropyrrole carboxylic acids. The synthesis uses a palladium-catalyzed allylation with the chiral Trost ligand as a key step for the construction of a quaternary chiral center. This allows the enantioselective conversion of 2-carboxy-3-hydroxy-pyrrole into 3-oxo-2,3-dihydropyrrole-2-allyl-2-carboxylate. The allyl group is subsequently converted into an aldehyde or ester group. Peptide coupling of the 3-oxo-2,3-dihydropyrrole amino acid leads to more extended systems with partially constrained dipeptide units.

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The 1H NMR coupling constant (3 J) between NH of the peptide bond and the α-CH shows a value of 5.9 Hz which indicates free rotation of the 3-oxo-2,3-dihydropyrrole moieties around the connecting single bond.