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The syntheses of 1-and 7-hydroxypyrrolizidin-3-ones are described via asymmetric catalytic hydrogenation or diastereoselective reduction of ketones as key steps. 2,7-Disubstituted pyrrolizidin-3-ones are also prepared. The second chiral center is created using stereoselective electrophilic amination or hydroxylation reactions.

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Fused pyrrole derivatives R 0160 β-Ketoesters Derived from Pyroglutamic Acid: New Entry to Hydroxylated Pyrrolizidinones. -The stereoselective catalytic hydrogenation of β-hydroxyesters (I) and (VII) is applied for the preparation of hydroxylated pyrrolizidinones (VI) and (XII). The use of RuBr2((S)-BINAP) allows to prepare the corresponding 7-epimers of compounds (VI) and (XII). -(LE BOUC, G.; THOMASSIGNY, C.; GRECK*, C.; Heterocycles 75 (2008) 10, 2541-2547; Inst. Lavoisier, CNRS, Univ. Versailles St. Quentin, F-78035 Versailles, Fr.; Eng.) -R. Staver 07-130