title: Dual gold catalysis: a novel synthesis of bicyclic and tricyclic pyrroles from N-propargyl ynamides.
abstract: Various N-propargyl ynamides were converted to bicylic and tricyclic pyrroles by the use of a cationic dual-activation gold catalyst. This reaction starts with the nucleophilic addition of a gold acetylide onto an ynamide triple bond at the β-position of the nitrogen atom. Thus, gold vinylidene is formed, and then a second cyclization takes place. The formation of the gold vinylidene is indicated by the evidence that not only aryl ynamides but also alkyl ynamides undergo C-H activation in these reactions.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Tokimizu
authors.forename: Marcel
authors.initials: M
authors.lastname: Wieteck
authors.forename: Matthias
authors.initials: M
authors.lastname: Rudolph
authors.forename: Shinya
authors.initials: S
authors.lastname: Oishi
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
authors.forename: A Stephen K
authors.initials: AS
authors.lastname: Hashmi
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D000577:Amides; D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; D006046:Gold