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Enantioselective Friedel–Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters

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Abstract

Enantioselective Friedel–Crafts C2-alkylation reactions of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters were developed by using the complexes of Cu(OTf)2 or Zn(OTf)2 with chiral bisoxazoline ligands. A range of chiral indole-containing trifluoromethylated α-hydroxyesters and cyclic α-aminoesters bearing quaternary stereogenic centers were afforded in good yields and excellent enantioselectivities (up to 99% ee) under mild conditions.

Graphical abstract: Enantioselective Friedel–Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters

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Publication details

The article was received on 11 Nov 2017, accepted on 12 Dec 2017 and first published on 13 Dec 2017


Article type: Research Article
DOI: 10.1039/C7QO01014A
Citation: Org. Chem. Front., 2018, Advance Article
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    Enantioselective Friedel–Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters

    B. Huang, L. Wu, R. Liu, L. Xing, R. Liang and Y. Jia, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO01014A

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