title: Brine-Stabilized 2,2,2-Trifluorodiazoethane and Its Application in the Synthesis of CF3-Substituted Cyclopropane α-Amino Acids.
abstract: A facile thermodynamic cyclopropanation of trisubstituted olefinic azlactones with a stock solution of CF3CHN2 in CH3CN is realized. This method shows excellent generality, affording a wide range of trifluoromethyl-substituted cyclopropanes bearing azlactone rings in good to high yields and diastereoselectivities. With the products in hand, the trifluoromethyl-substituted cyclopropane α-amino acids and relative peptide derivatives could be readily obtained.
authors.affiliation: Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China.
authors.forename: Chuan-Le
authors.initials: CL
authors.lastname: Zhu
authors.affiliation: Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China.
authors.forename: Li-Jun
authors.initials: LJ
authors.lastname: Yang
authors.affiliation: Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China.
authors.forename: Shen
authors.initials: S
authors.lastname: Li
authors.affiliation: Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Zheng
authors.affiliation: Department of Chemistry, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China.
authors.forename: Jun-An
authors.initials: JA
authors.lastname: Ma
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry*
chemical_list: C000592527:2,2,2-trifluorodiazoethane; D000596:Amino Acids; D001391:Azo Compounds; D003521:Cyclopropanes; D006845:Hydrocarbons, Fluorinated; D012492:Salts; C017082:brine; C030797:cyclopropane