title: Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes.
abstract: Synthesis of substituted 1,3-dienes was achieved via gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers. The N-heterocyclic carbene gold chloride catalyst (IPrAuCl) was superior in terms of activity and selectivity and afforded the 3,3-product in excellent yields. A proposed cation-π inter-action played a significant role in affecting the reaction rate.
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA. mek@chem.fsu.edu
authors.forename: Marie E
authors.initials: ME
authors.lastname: Krafft
authors.forename: Kassem M
authors.initials: KM
authors.lastname: Hallal
authors.forename: Dinesh V
authors.initials: DV
authors.lastname: Vidhani
authors.forename: John W
authors.initials: JW
authors.lastname: Cran
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D050607:Organogold Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D050607:Organogold Compounds; D014753:Vinyl Compounds; C100195:vinyl ether; D006046:Gold