title: Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.
abstract: The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization-cyclization followed by C3- to C2-alkyl migration and rearomatization.
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Michele
authors.initials: M
authors.lastname: Mari
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Simone
authors.initials: S
authors.lastname: Lucarini
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Bartoccini
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Giovanni
authors.initials: G
authors.lastname: Piersanti
authors.affiliation: Department of Biomolecular Sciences, University of Urbino "Carlo Bo", Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Gilberto
authors.initials: G
authors.lastname: Spadoni
keywords: Dehydroalanine; Friedel–Crafts alkylation; indoles; migration; tryptophans