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. 2018 May 15;16(19):3655-3661.
doi: 10.1039/c8ob00861b.

Regio- and stereospecific Friedel-Crafts alkylation of indoles with spiro-epoxyoxindoles

Guofeng Li  1 , Guangjun Bao, Gongming Zhu, Yiping Li, Liwu Huang, Wangsheng Sun, Liang Hong, Rui Wang
Affiliations

Regio- and stereospecific Friedel-Crafts alkylation of indoles with spiro-epoxyoxindoles

Guofeng Li et al. Org Biomol Chem. .

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.

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