title: Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.
abstract: Palladium(II)-catalyzed aerobic oxidative cyclization of alkenes with tethered tert-butanesulfinamides furnishes enantiopure 2,5-disubstituted pyrrolidines, originating from readily available and easily diversified starting materials. These reactions are the first reported examples of metal-catalyzed addition of sulfinamide nucleophiles to alkenes.
authors.affiliation: University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
authors.forename: Joanne E
authors.initials: JE
authors.lastname: Redford
authors.forename: Richard I
authors.initials: RI
authors.lastname: McDonald
authors.forename: Matthew L
authors.initials: ML
authors.lastname: Rigsby
authors.forename: Joshua D
authors.initials: JD
authors.lastname: Wiensch
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002073:Butanes; D011759:Pyrrolidines; D013449:Sulfonamides; C511422:tert-butanesulfinamide