title: Highly substituted enantioenriched cyclopentane derivatives by palladium-catalyzed [3 + 2] trimethylenemethane cycloadditions with disubstituted nitroalkenes.
abstract: β,β-Disubstituted nitroalkenes readily undergo palladium-catalyzed [3 + 2] cycloaddition with trimethylenemethane to generate nitrocyclopentanes in excellent yield and enantioselectivity. The reaction provides access to heavily substituted cyclopentanes containing up to three contiguous stereocenters, and the products may be converted to both cyclopentylamines and cyclopentenones. A rare dependence of the sense of chirality of the cycloadducts was observed to be exclusively dependent on the structure of the palladium-bound trimethylenemethane intermediate.
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Dustin A
authors.initials: DA
authors.lastname: Bringley
authors.forename: B Michael
authors.initials: BM
authors.lastname: O'Keefe
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003517:Cyclopentanes; D009574:Nitro Compounds; C522820:trimethylenemethane; D010165:Palladium; D008697:Methane