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Friedel–Crafts Alkylation of Indoles with p‑Quinols: The Role of Hydrogen Bonding of Water for the Desymmetrization of the Cyclohexadienone System

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journal contribution
posted on 18.04.2016, 17:33 authored by Carolina García-García, Laura Ortiz-Rojano, Susana Álvarez, Rosana Álvarez, María Ribagorda, M. Carmen Carreño
Lewis acid catalyzed Friedel–Crafts alkylation of indoles has been achieved in high yields and selectivities using p-quinols as electrophiles. (S)-Binol-3,3′-(9-anthracenyl)-phosphoric acid was able to catalyze the enantioselective formation of 5-(3-indole)-2-cyclohexenone derivatives. Experimental results and theoretical calculations explained the enantioselectivity based on a transition state where two water molecules act as a tether joining the p-quinol with the phosphoric acid and the NH of indole, thus facilitating the desymmetrization of the prochiral cyclohexadienone framework.