title: Chiral monofluorobenzyl carbanions: synthesis of enantiopure β-fluorinated β-phenylethylamines.
abstract: The preparation of a stabilized monofluorobenzyl carbanion by means of a remote homochiral sulfinyl group and its completely stereoselective reactions with N-p-tolylsulfinylimines are described. The use of these reactions followed by the simultaneous removal of both chiral auxiliaries with tBuLi, which occurs without epimerization at the benzylic position, provides the quickest entry to enantiomerically pure β-fluorinated β-phenylethylamines.
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es
authors.forename: José L García
authors.initials: JL
authors.lastname: Ruano
authors.forename: Alejandro
authors.initials: A
authors.lastname: Parra
authors.forename: Inés
authors.initials: I
authors.lastname: Alonso
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
authors.forename: Carlos
authors.initials: C
authors.lastname: del Pozo
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Arroyo
authors.forename: Ascensión
authors.initials: A
authors.lastname: Sanz-Tejedor
mesh_terms: D000838:Anions / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D054879:Halogenation; D007097:Imines / Q000737:chemistry*; D008968:Molecular Conformation; D010627:Phenethylamines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000838:Anions; D001593:Benzyl Compounds; D007097:Imines; D010627:Phenethylamines; C029261:phenethylamine