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Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines

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Abstract

An organocatalytic enantioselective functionalization in the carbocyclic ring of indoles with benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional organocatalyst. This aza-Friedel–Crafts reaction provides 4-indolyl, 5-indolyl and 7-indolyl sulfamidate derivatives in good yields (up to 99%) and with moderate to high enantioselectivities (up to 86% ee).

Graphical abstract: Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines

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Publication details

The article was received on 02 Nov 2018, accepted on 13 Nov 2018 and first published on 13 Nov 2018


Article type: Paper
DOI: 10.1039/C8NJ05577G
Citation: New J. Chem., 2019, Advance Article
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    Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines

    C. Vila, A. Tortosa, G. Blay, M. C. Muñoz and J. R. Pedro, New J. Chem., 2019, Advance Article , DOI: 10.1039/C8NJ05577G

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