title: Diastereo- and enantioselective conjugate addition of alpha-ketoesters to nitroalkenes catalyzed by a chiral Ni(OAc)(2) complex under mild conditions.
abstract: A highly efficient, catalytic, diastereo- and enantioselective conjugate addition of alpha-ketoesters to nitroalkenes has been devised. The reaction was applicable to various substrates. Notably, the combination of endogenous and exogenous bases was effective, allowing a small amount of the catalyst (0.1-1 mol % Ni) to promote the reaction efficiently. The synthetic utility of this reaction was demonstrated in the synthesis of substituted pyrrolidine derivatives, whose stereochemistry is closely related to biologically important natural products such as kainic acid.
authors.affiliation: RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors.forename: Ayako
authors.initials: A
authors.lastname: Nakamura
authors.forename: Sylvain
authors.initials: S
authors.lastname: Lectard
authors.forename: Daisuke
authors.initials: D
authors.lastname: Hashizume
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
authors.forename: Mikiko
authors.initials: M
authors.lastname: Sodeoka
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000475:Alkenes; D004952:Esters; D007659:Ketones; D009574:Nitro Compounds; D009532:Nickel