title: Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.
abstract: We report the generation of the first 3,4-piperidyne and its use as a building block for the synthesis of annulated piperidines. Experimental and computational studies of this intermediate are disclosed, along with comparisons to the well-known 3,4-pyridyne. The distortion/interaction model is used to explain the observed regioselectivities.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors.forename: Travis C
authors.initials: TC
authors.lastname: McMahon
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors.forename: Jose M
authors.initials: JM
authors.lastname: Medina
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors.forename: Yun-Fang
authors.initials: YF
authors.lastname: Yang
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors.forename: Bryan J
authors.initials: BJ
authors.lastname: Simmons
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
mesh_terms: D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D010880:Piperidines