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  • Title: Organocatalytic asymmetric synthesis of benzazepinoindole derivatives with trifluoromethylated quaternary stereocenters by chiral phosphoric acid catalysts.
    Author: Rahman A, Xie E, Lin X.
    Journal: Org Biomol Chem; 2018 Feb 21; 16(8):1367-1374. PubMed ID: 29406543.
    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.
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