title: Diastereoselective synthesis of 2-phenyl-3-(trifluoromethyl)piperazines as building blocks for drug discovery.
abstract: The synthesis of enantiomerically pure cis- and trans-2-phenyl-3-(trifluoromethyl)piperazines is described. It involved, as the key step, a diastereoselective nucleophilic addition of the Ruppert-Prakash reagent (TMSCF3) to α-amino sulfinylimines bearing Ellman's auxiliary. This methodology allows an entry into hitherto unknown trifluoromethylated and stereochemically defined piperazines, key scaffold components in medicinal chemistry.
authors.affiliation: Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe , E-46012 Valencia, Spain.
authors.forename: María
authors.initials: M
authors.lastname: Sánchez-Roselló
authors.forename: Oscar
authors.initials: O
authors.lastname: Delgado
authors.forename: Natalia
authors.initials: N
authors.lastname: Mateu
authors.forename: Andrés A
authors.initials: AA
authors.lastname: Trabanco
authors.forename: Michiel
authors.initials: M
authors.lastname: Van Gool
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
mesh_terms: D002384:Catalysis; D055808:Drug Discovery; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D010879:Piperazines; D012821:Silanes; C509472:trimethyl(trifluoromethyl)silane