Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 12, Issue 20, Pages 5376-5382Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200600192
Keywords
asymmetric hydrogenation; cyclization; gold; homogeneous catalysis; rhodium
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Different furyl-substituted (Z)-dehydroamino acid derivatives were hydrogenated with the rhodium/Mandyphos(OMe)-system to give enantiomeric excesses between 80 and 98%. The absolute configuration of the newly formed stereogenic center was determined by anomalous diffraction to be R. These chiral furyl alanines were transferred into 8-hydroxytetrahy-droisoquinolines by employing gold-catalyzed arene synthesis as the key step. During the latter reaction sequence, also including either a propargylation or a reduction, a protection of the hydroxy group, and a subsequent propargylation, no racemization of the stereogenic center was observed. With very electron-rich furans, instead of the 8-hydroxytetrahydroquinolines as products, furans anellated to seven-membered rings with exocyclic C-C double bonds are formed under the same reaction conditions.
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