title: Diastereoselective, Zinc-Catalyzed Alkynylation of α-Bromo Oxocarbenium Ions.
abstract: We have developed a bromination/alkynylation sequence that enables efficient transformation of simple cyclic enol ethers to difunctionalized products. The success of this strategy relies on a highly diastereselective, zinc-catalyzed addition of terminal alkynes to α-bromo oxocarbenium ions, formed in situ via ionization of acetal precursors. Using this method, trans-α-alkynyl-β-halo pyran and furan derivatives can be prepared with high diastereoselectivity and excellent functional group tolerance.
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
authors.forename: Tatsiana
authors.initials: T
authors.lastname: Haidzinskaya
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
authors.forename: Hilary A
authors.initials: HA
authors.lastname: Kerchner
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
authors.forename: Jixin
authors.initials: J
authors.lastname: Liu
authors.affiliation: Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
authors.forename: Mary P
authors.initials: MP
authors.lastname: Watson
mesh_terms: D000080:Acetals / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004988:Ethers, Cyclic / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry*
chemical_list: D000080:Acetals; D000480:Alkynes; D001965:Bromides; D004988:Ethers, Cyclic; D006842:Hydrocarbons, Brominated; D007477:Ions; D017967:Zinc Compounds; C093802:zinc bromide