title: Indium Tribromide Catalyzed Coupling Reaction of Enol Ethers with Silyl Ketene Imines toward the Synthesis of β,γ-Unsaturated Nitriles.
abstract: Herein, a coupling reaction of enol ethers with silyl ketene imines in the presence of catalytic amounts of InBr3 and Me3 SiBr is described. Kinetic studies have revealed that an indium catalyst and Me3 SiBr accelerated the coupling process and the regeneration of the catalyst, respectively. Various types of enol ethers and silyl ketene imines are applicable. In addition, a formal synthesis of verapamil was achieved by using this novel coupling reaction.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan). nishimoto@chem.eng.osaka-u.ac.jp.|Frontier Research Base for Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan). nishimoto@chem.eng.osaka-u.ac.jp.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Nishimoto
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan).
authors.forename: Takashi
authors.initials: T
authors.lastname: Nishimura
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 (Japan). yasuda@chem.eng.osaka-u.ac.jp.
authors.forename: Makoto
authors.initials: M
authors.lastname: Yasuda
keywords: cross-coupling; enol ethers; indium; silicon; silyl ketene imines