title: Catalytic desymmetrization of cyclohexadienes by asymmetric bromolactonization.
abstract: Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic cyclic ene-carboxylic acid, where the starting material was recovered with high enantioselectivity.
authors.affiliation: School of Pharmaceutical Science, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Kazutada
authors.initials: K
authors.lastname: Ikeuchi
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Ido
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yoshimura
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Asakawa
authors.forename: Makoto
authors.initials: M
authors.lastname: Inai
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
mesh_terms: D002384:Catalysis; D053138:Cyclohexenes / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D053138:Cyclohexenes; D006842:Hydrocarbons, Brominated; D007783:Lactones; C048401:1,4-cyclohexadiene