title: Asymmetric Conjugate Addition of Benzofuran-2-ones to Alkyl 2-Phthalimidoacrylates: Modeling Structure-Stereoselectivity Relationships with Steric and Electronic Parameters.
abstract: A highly predictive model to correlate the steric and electronic parameters of tertiary amine thiourea catalysts with the stereoselectivity of Michael reactions of 3-substituted benzofuranones and alkyl 2-phthalimidoacrylates is described. As predicted, new 3,5-bis(trifluoromethyl)benzyl- and methyl-substituted tertiary amine thioureas turned out to be highly suitable catalysts for this reaction and enabled the synthesis of enantioenriched α-amino acid derivatives with 1,3-nonadjacent stereogenic centers.
authors.affiliation: State Key Laboratory of Elemento-organic Chemistry, Department of Chemistry, Nankai University, and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, China.
authors.forename: Chen
authors.initials: C
authors.lastname: Yang
authors.affiliation: State Key Laboratory of Elemento-organic Chemistry, Department of Chemistry, Nankai University, and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, China.
authors.forename: En-Ge
authors.initials: EG
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Elemento-organic Chemistry, Department of Chemistry, Nankai University, and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, China. xin_li@nankai.edu.cn.
authors.forename: Xin
authors.identifier: 0000-0001-6020-9170
authors.initials: X
authors.lastname: Li
authors.affiliation: State Key Laboratory of Elemento-organic Chemistry, Department of Chemistry, Nankai University, and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, China. chengjp@nankai.edu.cn.
authors.forename: Jin-Pei
authors.initials: JP
authors.lastname: Cheng
keywords: amino acids; asymmetric catalysis; enantioselectivity; free-energy relationships; hydrogen bonds