title: A single step approach to piperidines via Ni-catalyzed β-carbon elimination.
abstract: An easy and expeditious route to substituted piperidines is described. A Ni-phosphine complex was used as catalyst for [4 + 2] cycloaddition of 3-azetidinone and alkynes. The reaction has broad substrate scope and affords piperidines in excellent yields and excellent regioselectivity. In the reaction of an enantiopure azetidinone, complete retention of stereochemistry was observed.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84102, USA.
authors.forename: Puneet
authors.initials: P
authors.lastname: Kumar
authors.forename: Janis
authors.initials: J
authors.lastname: Louie
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008698:Mesylates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001555:Benzene Derivatives; D008698:Mesylates; D017646:Organosilicon Compounds; D010880:Piperidines; C524146:benzyne; D009532:Nickel