Regio- and stereospecific Friedel-Crafts alkylation of indoles with spiro-epoxyoxindolesElectronic supplementary information (ESI) available: Details of the experimental procedure, data, HPLC and NMR spectra of all compounds. See DOI: 10.1039/c8ob00861b

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/H 2 O (1 : 9) without the use of catalysts. This protocol provides an atomically economical, catalyst-free and simple route fo...

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Main Authors: Li, Guofeng, Bao, Guangjun, Zhu, Gongming, Li, Yiping, Huang, Liwu, Sun, Wangsheng, Hong, Liang, Wang, Rui
Format: Article
Language:English
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Summary: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/H 2 O (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. 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/H 2 O (1 : 9) without the use of catalysts.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00861b