title: Synthesis of enantiomerically pure anti-1,2-diaryl and syn-1,2-alkylaryl vic-selenoamines.
abstract: Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 °C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl[or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es
authors.forename: José L
authors.initials: JL
authors.lastname: García Ruano
authors.forename: Esther
authors.initials: E
authors.lastname: Torrente
authors.forename: Inés
authors.initials: I
authors.lastname: Alonso
authors.forename: Mercedes
authors.initials: M
authors.lastname: Rodriguez
authors.forename: Ana M
authors.initials: AM
authors.lastname: Martín-Castro
authors.forename: Alessandro
authors.initials: A
authors.lastname: Degl'Innocenti
authors.forename: Lucrezia
authors.initials: L
authors.lastname: Frateschi
authors.forename: Antonella
authors.initials: A
authors.lastname: Capperucci
mesh_terms: D007097:Imines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D010627:Phenethylamines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D007097:Imines; D016566:Organoselenium Compounds; D010627:Phenethylamines; D014105:Tosyl Compounds; D014269:Trifluoroacetic Acid; D000432:Methanol