title: Three-component domino process for the pyrrolizine skeleton via [3 + 2]-cycloaddition-enamine cyclization triggered by a gold catalyst.
abstract: Pyrrolizines are bicyclic fused azaheterocycles with a bridgehead nitrogen contained in a core skeleton and are often found in biologically active compounds. Despite their importance, there have been few reports on concise and flexible syntheses of pyrrolizines. A novel one-pot, convergent method is described for pyrrolizines by simple mixing of iminoesters, acetylenes, and dipolarophiles in the presence of a cationic gold catalyst and an acid additive. This domino process affords multisubstituted pyrrolizines without handling unstable intermediates.
authors.affiliation: Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama , 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Sugimoto
authors.forename: Nozomi
authors.initials: N
authors.lastname: Yamamoto
authors.forename: Daisuke
authors.initials: D
authors.lastname: Tominaga
authors.forename: Yuji
authors.initials: Y
authors.lastname: Matsuya
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D061565:Cycloaddition Reaction; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D011758:Pyrroles; D006046:Gold