Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 5, Pages 1664-1669Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902355
Keywords
alkylation; asymmetric catalysis; dioxides; chalcones; scandium
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Funding
- National Natural Science Foundation of China [20732003, 20602025]
- Ministry of Education [20070610019]
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A highly enantioselective Friedel-Crafts (F-C) alkylation of indoles and pyrrole with chalcone derivatives catalyzed by a chiral N,N'-dioxide-Sc(OTf)(3) complex has been developed that tolerates a wide range of substrates. The reaction proceeds in moderate to excellent yields and high enantioselectivities (85-92% enantiomeric excess) using 2mol% (for indole) or 0.5 mol% (for pyrrole) catalyst loading, which showed the potential value of the catalyst system. Meanwhile, a strong positive nonlinear effect was observed. On the basis of the experimental results and previous reports, a possible working model is proposed to explain the origin of the activation and asymmetric induction.
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