title: Amide and amine nucleophiles in polar radical crossover cycloadditions: synthesis of γ-lactams and pyrrolidines.
abstract: In this work we present a direct catalytic synthesis of γ-lactams and pyrrolidines from alkenes and activated unsaturated amides or protected unsaturated amines, respectively. Using a mesityl acridinium single electron photooxidant and a thiophenol cocatalyst under irradiation, we are able to directly forge these important classes of heterocycles with complete regiocontrol.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Nathan J
authors.initials: NJ
authors.lastname: Gesmundo
authors.forename: Jean-Marc M
authors.initials: JM
authors.lastname: Grandjean
authors.forename: David A
authors.initials: DA
authors.lastname: Nicewicz
mesh_terms: D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D055668:Photochemical Processes; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D000588:Amines; D007769:Lactams; D010636:Phenols; D011759:Pyrrolidines; D013438:Sulfhydryl Compounds; C042983:thiophenol