title: Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation.
abstract: α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
authors.forename: Fedor
authors.initials: F
authors.lastname: Romanov-Michailidis
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
authors.forename: Kassandra F
authors.initials: KF
authors.lastname: Sedillo
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
authors.forename: Jamie M
authors.initials: JM
authors.lastname: Neely
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004095:Dihydropyridines; D010091:Oximes; C038806:1,4-dihydropyridine; D012238:Rhodium