title: Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes.
abstract: The dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under Rh(III) catalysis. These reactions are successful using Cu(OAc)2 or air as the stoichiometric oxidant, and provide spirocyclic enones, the basic ring system of which appears in several natural products. Application of this process to the preparation of a highly functionalized tetracycle is also demonstrated.
authors.affiliation: EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh, EH9 3 JJ (UK) and School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK).
authors.forename: Szymon
authors.initials: S
authors.lastname: Kujawa
authors.forename: Daniel
authors.initials: D
authors.lastname: Best
authors.forename: David J
authors.initials: DJ
authors.lastname: Burns
authors.forename: Hon Wai
authors.initials: HW
authors.lastname: Lam
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000480:Alkynes; D012238:Rhodium
keywords: CH activation; alkyne; enyne; phenol; rhodium