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Synlett 1998; 1998(6): 649-651
DOI: 10.1055/s-1998-1724
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The First Stereoselective Bifunctionalization of 4-Quinolones with Organometallics and N-Halosuccinimides to 2,3-trans Disubstituted Tetrahydroquinolones: Expected and Unexpected Results

Uwe Beifuss* , Gerald Feder, Teresa Bes, Isabel Usón
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany; Fax + 49(5 51)39 96 60; E-mail: ubeifus@gwdg.de
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Publication Date:
31 December 2000 (online)

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The C-2-addition of organometallic reagents to 4-quinolones followed by reaction with N-halosuccinimides provides a short and diastereoselective entry for the preparation of 2,3-trans disubstituted tetrahydroquinolones.

organolithium reagents - Grignard reagents - C-2 addition - halogenation - quinolones