title: Synthesis of trans-cycloalkenes via enantioselective cyclopropanation and skeletal rearrangement.
abstract: An efficient one-pot two-step procedure for asymmetric synthesis of piperidine-fused trans-cycloalkenes is reported. The method comprises the initial enantioselective installation of another cyclopropane ring onto methylenecyclopropanes and the subsequent thermal skeletal rearrangement in which the installed and inherent cyclopropane rings are both opened. A concerted mechanism is proposed for the latter thermal rearrangement reaction together with a closed transition state model.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University , Katsura, Kyoto 615-8510, Japan.
authors.forename: Tomoya
authors.initials: T
authors.lastname: Miura
authors.forename: Takayuki
authors.initials: T
authors.lastname: Nakamuro
authors.forename: Chia-Jung
authors.initials: CJ
authors.lastname: Liang
authors.forename: Masahiro
authors.initials: M
authors.lastname: Murakami