title: Preparation of optically pure α-trifluoromethyl-α-amino acids from N-tosyl-2-trifluoromethyl-2-alkyloxycarbonyl aziridine.
abstract: The preparation of optically pure α-trifluoromethyl-α-amino acids from N-tosyl-2-trifluoromethyl-2-alkyloxycarbonylaziridine is described. Optically pure aziridine was prepared with a 60% yield via three steps from optically pure 2,3-epoxy-1,1,1-trifluoropropane (TFPO). Ring-opening reactions of the aziridine with a variety of nucleophiles and subsequent deprotection of the N-tosyl moieties gave the optically pure β-substituted-α-trifluoromethyl-α-amino acids in moderate to good yields (up to 85%) without racemization at the quaternary stereogenic center of the amino acid.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama, 700-8530, Japan. tkata@cc.okayama-u.ac.jp
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Katagiri
authors.forename: Yousuke
authors.initials: Y
authors.lastname: Katayama
authors.forename: Mayuko
authors.initials: M
authors.lastname: Taeda
authors.forename: Takanori
authors.initials: T
authors.lastname: Ohshima
authors.forename: Naomi
authors.initials: N
authors.lastname: Iguchi
authors.forename: Kenji
authors.initials: K
authors.lastname: Uneyama
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: C570128:2,3-epoxy-1,1,1-trifluoropropane; D000596:Amino Acids; D001388:Aziridines; D004852:Epoxy Compounds; D006845:Hydrocarbons, Fluorinated; D014105:Tosyl Compounds; C033132:aziridine