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Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 3356067
Author(s) Pauli, Larissa; Tannert, René; Scheil, Robin; Pfaltz, Andreas
Author(s) at UniBasel Pfaltz, Andreas
Year 2015
Title Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts
Journal Chemistry : a European journal
Volume 21
Number 4
Pages / Article-Number 1482-7
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.
Publisher Wiley
ISSN/ISBN 1521-3765
edoc-URL http://edoc.unibas.ch/40542/
Full Text on edoc No
Digital Object Identifier DOI 10.1002/chem.201404903
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/25394881
ISI-Number WOS:000347841500017
Document type (ISI) Journal Article
 
   

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