title: Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling.
abstract: Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2(-) is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University , Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.forename: Yuta
authors.initials: Y
authors.lastname: Murai
authors.forename: Takuma
authors.initials: T
authors.lastname: Yoshida
authors.forename: Akiko
authors.initials: A
authors.lastname: Ishida
authors.forename: Katsuyoshi
authors.initials: K
authors.lastname: Masuda
authors.forename: Yasuko
authors.initials: Y
authors.lastname: Sakihama
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Hashidoko
authors.forename: Yasumaru
authors.initials: Y
authors.lastname: Hatanaka
authors.forename: Makoto
authors.initials: M
authors.lastname: Hashimoto
mesh_terms: D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry; D003978:Diazomethane / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D019920:Photoaffinity Labels
chemical_list: C024282:3-trifluoromethyl-3-phenyldiazirine; D001389:Azirines; D006845:Hydrocarbons, Fluorinated; D010091:Oximes; D019920:Photoaffinity Labels; D010649:Phenylalanine; D003978:Diazomethane