title: Palladium-catalyzed dearomative trimethylenemethane cycloaddition reactions.
abstract: A general protocol for the palladium-catalyzed dearomative trimethylenemethane [3+2] cycloaddition reaction with simple nitroarene substrates is described. This methodology leads to the exclusive formation of the dearomatized alicyclic products without subsequent rearomatization. The reaction is tolerant toward a broad range of heterocyclic and benzenoid substrates. The use of chiral bisdiamidophosphite ligands enabled the development of an enantioselective variant of this transformation, representing one of the rare examples of an asymmetric catalytic dearomatization process.
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Veronika
authors.initials: V
authors.lastname: Ehmke
authors.forename: B Michael
authors.initials: BM
authors.lastname: O'Keefe
authors.forename: Dustin A
authors.initials: DA
authors.lastname: Bringley
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009600:Nitroquinolines / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006841:Hydrocarbons, Aromatic; D008024:Ligands; D009600:Nitroquinolines; C522820:trimethylenemethane; D010165:Palladium; C089803:5-nitroquinoline; D008697:Methane