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The electrophilic intermediate, vinylogous imine or vinylogous iminium, can be in situ generated from 3-indolylmethanols under acidic conditions. With the aid of chiral catalysts, miscellaneous nucleophiles can attack these electrophilic intermediates to afford enantioenriched and biologically important 3-substituted indole derivatives. The recent advances of preparation of optically active indole derivatives from 3-indolylmethanols via asymmetric alkylation, asymmetric reduction and asymmetric rearrangement are summarized.doi:10.6023/cjoc201510024 fatcat:7mgpkrdw4jbwrahq6q3vdd7sia