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Issue 74, 2012
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Highly enantioselective Friedel–Crafts alkylation of indoles and pyrrole with β,γ-unsaturated α-ketoesters catalyzed by heteroarylidene-tethered bis(oxazoline) copper complexes

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Abstract

The simple and cheap chiral catalyst, heteroarylidene-tethered Ph-bis(oxazoline)–Cu(OTf)2, can efficiently catalyze the asymmetric F–C alkylation of indoles and pyrrole with β,γ-unsaturated α-ketoesters. The 3-indolyl adducts were obtained in up to >99% ee. Moreover, the 2-pyrrolyl adducts were achieved in up to 92% ee for the first time.

Graphical abstract: Highly enantioselective Friedel–Crafts alkylation of indoles and pyrrole with β,γ-unsaturated α-ketoesters catalyzed by heteroarylidene-tethered bis(oxazoline) copper complexes

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Publication details

The article was received on 05 Jul 2012, accepted on 26 Jul 2012, published on 26 Jul 2012 and first published online on 26 Jul 2012


Article type: Communication
DOI: 10.1039/C2CC34803A
Citation: Chem. Commun., 2012,48, 9281-9283
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    Highly enantioselective Friedel–Crafts alkylation of indoles and pyrrole with β,γ-unsaturated α-ketoesters catalyzed by heteroarylidene-tethered bis(oxazoline) copper complexes

    L. Liu, H. Ma, Y. Xiao, F. Du, Z. Qin, N. Li and B. Fu, Chem. Commun., 2012, 48, 9281
    DOI: 10.1039/C2CC34803A

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