title: Regioselective cycloaddition of 3-azetidinones and 3-oxetanones with alkynes through nickel-catalysed carbon-carbon bond activation.
abstract: Get in the ring! The first examples of transition-metal-catalysed C-C bond activation of 3-azetidinones and 3-oxetanones are reported. In the presence of a nickel catalyst and alkynes, a regioselective and high-yielding [4+2] cycloaddition occurs, leading to the formation of pyridinones, pyranones and eventually 4,5-disubstituted 3-hydroxypyridines (see scheme).
authors.affiliation: Department of Chemistry, University of Liverpool, Crown Street, Liverpool L69 7ZD, UK.
authors.forename: Kelvin Y T
authors.initials: KY
authors.lastname: Ho
authors.forename: Christophe
authors.initials: C
authors.lastname: Aïssa
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010647:Phenyl Ethers / Q000737:chemistry*; D013237:Stereoisomerism; D028561:Transition Elements / Q000737:chemistry*
chemical_list: C116379:2-azetidinone; D000480:Alkynes; D001384:Azetidines; D010647:Phenyl Ethers; D028561:Transition Elements; D009532:Nickel