title: Enantioselective Michael addition/iminium ion cyclization cascades of tryptamine-derived ureas.
abstract: A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, U.K.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Aillaud
authors.forename: David M
authors.initials: DM
authors.lastname: Barber
authors.forename: Amber L
authors.initials: AL
authors.lastname: Thompson
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007477:Ions / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*; D014508:Urea / Q000737:chemistry*
chemical_list: C406944:BINOL, naphthol; D006571:Heterocyclic Compounds; D007477:Ions; D009284:Naphthols; D010756:Phosphoric Acids; D014363:Tryptamines; C030820:tryptamine; D014508:Urea; C030242:phosphoric acid