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Issue 8, 2018
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Organocatalytic asymmetric synthesis of benzazepinoindole derivatives with trifluoromethylated quaternary stereocenters by chiral phosphoric acid catalysts

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Abstract

An enantioselective aza-Friedel–Crafts reaction of trifluoromethyl dihydrobenzoazepinoindoles with pyrroles catalyzed by a chiral spirocyclic phosphoric acid was developed. This methodology provides a facile route to CF3- and pyrrole-containing benzazepinoindoles bearing quaternary stereocenters in good yields and with moderate to excellent enantioselectivities (up to 93% ee). Indoles were also investigated as electron-rich aromatic substrates to afford the corresponding chiral heterocycles with good yields and considerable enantioselectivities. The introduction of CF3 shows a remarkable fluorine effect and increases the activation and stereoinduction.

Graphical abstract: Organocatalytic asymmetric synthesis of benzazepinoindole derivatives with trifluoromethylated quaternary stereocenters by chiral phosphoric acid catalysts

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Publication details

The article was received on 08 Jan 2018, accepted on 29 Jan 2018 and first published on 29 Jan 2018


Article type: Paper
DOI: 10.1039/C8OB00055G
Citation: Org. Biomol. Chem., 2018,16, 1367-1374
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    Organocatalytic asymmetric synthesis of benzazepinoindole derivatives with trifluoromethylated quaternary stereocenters by chiral phosphoric acid catalysts

    A. Rahman, E. Xie and X. Lin, Org. Biomol. Chem., 2018, 16, 1367
    DOI: 10.1039/C8OB00055G

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