title: Synthesis of tetrahydro-β-carbolines via isomerization of N-allyltryptamines: a metal-catalyzed variation on the Pictet-Spengler theme.
abstract: An efficient and broadly applicable alternative to the classical Pictet-Spengler synthesis of tetrahydro-β-carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile.
authors.affiliation: Department of Chemistry, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Erhad
authors.initials: E
authors.lastname: Ascic
authors.forename: Casper L
authors.initials: CL
authors.lastname: Hansen
authors.forename: Sebastian T
authors.initials: ST
authors.lastname: Le Quement
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Nielsen
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis*; D002243:Carbolines / Q000138:chemical synthesis*; D002384:Catalysis; D056831:Coordination Complexes; D003500:Cyclization; D007211:Indoles / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D002243:Carbolines; D056831:Coordination Complexes; D007211:Indoles; D014363:Tryptamines; C009804:tryptoline