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Issue 11, 2011
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Asymmetric synthesis of chiral trifluoromethylated heliotridane via highly catalytic asymmetric Friedel–Crafts alkylation with β-trifluoromethylated acrylates and pyrroles

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Abstract

Chiral Ph-dbfox (Ph-dbfox = (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline))/Zn(NTf2)2 catalyzed enantioselective Friedel–Crafts reactions of β-CF3 acrylates with pyrroles and indoles have been investigated, which afforded the corresponding chiral trifluoromethyl pyrrole and indole derivatives in high yields (90–99%) with a range of 66–99% ee values. With the aid of the chiral adduct of the asymmetric Friedel–Crafts reaction, the chiral trifluoromethylated heliotridane has been successfully constructed in good total yield.

Graphical abstract: Asymmetric synthesis of chiral trifluoromethylated heliotridane via highly catalytic asymmetric Friedel–Crafts alkylation with β-trifluoromethylated acrylates and pyrroles

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Publication details

The article was received on 22 Jun 2011, accepted on 15 Aug 2011 and first published on 08 Sep 2011


Article type: Paper
DOI: 10.1039/C1NJ20550A
New J. Chem., 2011,35, 2614-2621

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    Asymmetric synthesis of chiral trifluoromethylated heliotridane via highly catalytic asymmetric Friedel–Crafts alkylation with β-trifluoromethylated acrylates and pyrroles

    Y. Huang, S. Suzuki, G. Liu, E. Tokunaga, M. Shiro and N. Shibata, New J. Chem., 2011, 35, 2614
    DOI: 10.1039/C1NJ20550A

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