title: Catalytic Activity of epi-Quinine-Derived 3,5-Bis(trifluoromethyl)benzamide in Asymmetric Nitro-Michael Reaction of Furanones.
abstract: High catalytic activity of novel epi-quinine-derived 3,5-bis(CF3)benzamide in the asymmetric nitro-Michael reaction is described. With 0.1-5 mol % loadings of this catalyst, the addition of 5-substituted 2(3-H)-furanones to a wide range of nitroalkenes involving challenging substrates, β-alkylnitroalkenes, smoothly proceeded, giving the Michael adducts in high yields (>90%) with excellent diastereo- and enantioselectivity (>98:2 dr, syn major; 88-98% ee). DFT calculation was carried out to account for the high catalytic activity.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka City University, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Sekikawa
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka City University, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kitaguchi
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka City University, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Hayato
authors.initials: H
authors.lastname: Kitaura
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka City University, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Minami
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka City University, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Hatanaka