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

Date Issued
2015-01-01
Author(s)
Pauli, Larissa
Tannert, René
Scheil, Robin
Pfaltz, Andreas  
DOI
10.1002/chem.201404903
Abstract
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.
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