title: Multicomponent synthesis of pyrroles from cyclopropanes: a one-pot palladium(0)-catalyzed dehydrocarbonylation/dehydration.
abstract: Ring the changes: The cycloaddition of nitrones with 1-carboallyloxy-1-carbomethoxycyclopropanes yields tetrahydro-1,2-oxazines, which in turn undergo a Tsuji dehydrocarbonylation to give dihydro-1,2-oxazines (see scheme; dba = dibenzylideneacetone). Addition of base to this reaction mixture results in clean conversion to pyrroles. The result is a flexible three-component strategy for the synthesis of tetrasubstituted pyrroles.
authors.affiliation: Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada.
authors.forename: William J
authors.initials: WJ
authors.lastname: Humenny
authors.forename: Polydoros
authors.initials: P
authors.lastname: Kyriacou
authors.forename: Katarina
authors.initials: K
authors.lastname: Sapeta
authors.forename: Avedis
authors.initials: A
authors.lastname: Karadeolian
authors.forename: Michael A
authors.initials: MA
authors.lastname: Kerr
mesh_terms: D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D003681:Dehydration; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D009942:Organometallic Compounds; D011758:Pyrroles; D010165:Palladium