title: Synergistic Catalysis: Metal/Proton-Catalyzed Cyclization of Alkynones Toward Bicyclo[3.n.1]alkanones.
abstract: A highly efficient and practical synergistically metal/proton-catalyzed Conia-ene reaction for the synthesis of bicyclo[3.n.1]alkanones has been developed. This synergistic catalysis was successfully utilized in modifying natural compounds such as methyl dihydrojasmonate, α,β-thujone, and 5α-cholestan-3-one. Furthermore, the bridged carbonyl group of bicyclo[3.2.1]alkanones could be easily attacked by nucleophiles to give the ring-opened cycloheptenone products or bicyclo[4.2.1]amide in excellent yields. These reactions provide rapid access to a diverse range of cyclic structures from simple starting materials or naturally occurring compounds.
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China). zhusf@scut.edu.cn.
authors.forename: Shifa
authors.initials: S
authors.lastname: Zhu
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China).
authors.forename: Qiaohui
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China).
authors.forename: Kai
authors.initials: K
authors.lastname: Chen
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640 (P.R. China).
authors.forename: Huanfeng
authors.initials: H
authors.lastname: Jiang
keywords: Conia-ene reaction; bicyclo[3.n.1]alkanones; cycloheptanone; enolization; synergistic catalysis