title: Organocatalytic tail-to-tail dimerization of olefin: umpolung of methyl methacrylate mediated by N-heterocyclic carbene.
abstract: Highly selective tail-to-tail dimerization of methyl methacrylate has been realized by an N-heterocyclic carbene catalyst, giving dimethyl 2,5-dimethyl-2-hexenedioate with an E/Z ratio of 95:5 in 86% isolated yield. The umpolung mechanism is proposed on the basis of interception of the intermediates using ESI-MS analyses and deuterium-labeling experiments.
authors.affiliation: Department of Materials Science and Engineering, Nagoya Institute of Technology, Nagoya 466-8555, Japan. matsuoka.shinichi@nitech.ac.jp
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Matsuoka
authors.forename: Yoshiya
authors.initials: Y
authors.lastname: Ota
authors.forename: Atsushi
authors.initials: A
authors.lastname: Washio
authors.forename: Akiho
authors.initials: A
authors.lastname: Katada
authors.forename: Kenji
authors.initials: K
authors.lastname: Ichioka
authors.forename: Koji
authors.initials: K
authors.lastname: Takagi
authors.forename: Masato
authors.initials: M
authors.lastname: Suzuki