title: Friedel-Crafts Alkylation of Indoles with p-Quinols: The Role of Hydrogen Bonding of Water for the Desymmetrization of the Cyclohexadienone System.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid , C/Francisco Tomás y Valiente n° 7, Cantoblanco, 28049 Madrid, Spain.
authors.forename: Carolina
authors.initials: C
authors.lastname: García-García
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid , C/Francisco Tomás y Valiente n° 7, Cantoblanco, 28049 Madrid, Spain.
authors.forename: Laura
authors.initials: L
authors.lastname: Ortiz-Rojano
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidade de Vigo, CINBIO , Lagoas-Marcosende s/n, 36310 Vigo, Spain.
authors.forename: Susana
authors.initials: S
authors.lastname: Álvarez
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidade de Vigo, CINBIO , Lagoas-Marcosende s/n, 36310 Vigo, Spain.
authors.forename: Rosana
authors.initials: R
authors.lastname: Álvarez
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid , C/Francisco Tomás y Valiente n° 7, Cantoblanco, 28049 Madrid, Spain.
authors.forename: María
authors.initials: M
authors.lastname: Ribagorda
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid , C/Francisco Tomás y Valiente n° 7, Cantoblanco, 28049 Madrid, Spain.
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño