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Note | Regular issue | Vol 75, No. 10, 2008, pp.2541-2547
Published online, 2nd June, 2008
DOI: 10.3987/COM-08-11418
β-Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones

Géraldine Le Bouc, Christine Thomassigny, and Christine Greck*

*Université de Versailles St-Quentin-en-Yvelines, Institut Lavoisier de Versailles-UMR CNRS 8180, 45 Av. des Etats Unis, 78035 Versailles CEDEX, France

Abstract

Four hydroxylated pyrrolizidinones have been obtained from β-ketoesters derived from L-pyroglutamic acid or 4-(R)-hydroxy-L-pyroglutamic acid. The asymmetric hydrogenations, in the presence of BinapRuBr2 catalysts, of such β-ketoesters bearing pyrrolidinones proceeded with high diastereomeric excesses leaving to a complete control of the absolute configuration at the C7 hydroxylated carbon atom of the azabicycles.