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Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts.
Journal article

Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts.

  • 2014-11-15
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2015
N,P ligands
asymmetric catalysis
benzofurans
furans
iridium
Benzofurans
Catalysis
Furans
Hydrogenation
Iridium
Organophosphorus Compounds
Pyridines
Stereoisomerism
English Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubstituted furans proved to be more difficult substrates. The best results (80-97% conversion, 65-82% enantiomeric excess) were obtained with monosubstituted 2-alkylfurans and 2-[4-(trifluoromethyl)phenyl]furan. Benzofurans with an alkyl substituent at the 2- or 3-position also gave high conversions and enantioselectivity, whereas 2-aryl derivatives showed essentially no reactivity. The asymmetric hydrogenation of a 3-methylbenzofuran derivative was used as a key step in the formal total synthesis of the cytotoxic naphthoquinone natural product (-)-thespesone.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.rero.ch/global/documents/232069
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