Abstract
A highly enantioselective intermolecular addition of indoles to cyclic N-acyliminium ions catalyzed by thiourea Schiff base 1 is presented. Electron-rich and electron-deficient indole nucleophiles are suitable substrates for this transformation. For electron-rich indoles TMSCl is used as an additive, whereas for the addition of electron-deficient indoles BCl3 turned out to be a more efficient additive. A catalytic cycle is proposed, where chlorolactam 2 is anticipated as the actual substrate in the alkylation.
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