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Issue 19, 2018
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Regio- and stereospecific Friedel–Crafts alkylation of indoles with spiro-epoxyoxindoles

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Abstract

A highly efficient strategy for the regio- and stereospecific Friedel–Crafts alkylation of indoles with spiro-epoxyoxindoles has been developed in the mixed solvents of HFIP/H2O (1 : 9) without the use of catalysts. This protocol provides an atomically economical, catalyst-free and simple route for the construction of synthetically useful 3-(3-indolyl)-oxindole-3-methanols in high yields. Starting from optically active spiro-epoxyoxindoles a variety of enantiospecific 3-(3-indolyl)-oxindole-3-methanols could be obtained in high yields with complete retention of enantioselectivity.

Graphical abstract: Regio- and stereospecific Friedel–Crafts alkylation of indoles with spiro-epoxyoxindoles

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Publication details

The article was received on 12 Apr 2018, accepted on 24 Apr 2018 and first published on 24 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00861B
Citation: Org. Biomol. Chem., 2018,16, 3655-3661
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    Regio- and stereospecific Friedel–Crafts alkylation of indoles with spiro-epoxyoxindoles

    G. Li, G. Bao, G. Zhu, Y. Li, L. Huang, W. Sun, L. Hong and R. Wang, Org. Biomol. Chem., 2018, 16, 3655
    DOI: 10.1039/C8OB00861B

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