title: Brønsted acid catalyzed enantioselective α-amidoalkylation in the synthesis of isoindoloisoquinolines.
abstract: The Parham cyclization-intermolecular α-amidoalkylation sequence results in the facile enantioselective synthesis of 12b-substituted isoindoloisoquinolines (ee up to 95%) using BINOL-derived Brønsted acids. α-Amidoalkylation of indole occurs through the formation of a chiral conjugate base/bicyclic quaternary N-acyliminium ion pair.
authors.affiliation: Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, Apdo. 644, 48080 Bilbao, Spain.
authors.forename: Eider
authors.initials: E
authors.lastname: Aranzamendi
authors.forename: Nuria
authors.initials: N
authors.lastname: Sotomayor
authors.forename: Esther
authors.initials: E
authors.lastname: Lete
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C406944:BINOL, naphthol; D007211:Indoles; D007546:Isoquinolines; D009284:Naphthols