title: Asymmetric synthesis of 2-arylpiperazines.
abstract: An asymmetric synthesis of 2-arylpiperazines starting from phenacyl bromides, a variety of which are easily available, has been established. The synthesis features a CBS reduction of phenacyl bromide to provide optically enriched compounds, an SN2 reaction of 1,2,3-oxathiazolidine 2-oxides with an azide anion with invert of configuration, and construction of the piperazine ring via reduction of piperazine-2,3-diones.
authors.affiliation: Research Division, Mitsubishi Tanabe Pharma Corporation, Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan. Electronic address: yokosima@ps.nagoya-u.ac.jp.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yokoshima
authors.affiliation: Research Division, Mitsubishi Tanabe Pharma Corporation, Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan. Electronic address: Watanabe.Kazutoshi@mb.mt-pharma.co.jp.
authors.forename: Kazutoshi
authors.initials: K
authors.lastname: Watanabe
authors.affiliation: Research Division, Mitsubishi Tanabe Pharma Corporation, Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan.
authors.forename: Fumiaki
authors.initials: F
authors.lastname: Uehara
authors.affiliation: Research Division, Mitsubishi Tanabe Pharma Corporation, Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Usui
authors.affiliation: Research Division, Mitsubishi Tanabe Pharma Corporation, Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tanaka
mesh_terms: D000098:Acetophenones / Q000737:chemistry; D054659:Diketopiperazines / Q000737:chemistry; D007536:Isomerism; D010084:Oxidation-Reduction; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000098:Acetophenones; D054659:Diketopiperazines; D010879:Piperazines; C013190:phenacyl bromide
keywords: Asymmetric synthesis; Heterocycles; Piperazines