title: Diastereoselective addition of enantiopure lithium tert-butylsulfinylferrocene to imines.
abstract: (S)-tert-Butylsulfinylferrocene was submitted to ortho-metalation, and the corresponding lithium derivative was trapped by alkyl or aryl imines bearing various electron-withdrawing groups on the nitrogen atom (Ts, Dpp, Boc). New aminosulfoxides were obtained with complete diastereocontrol when Dpp or Boc groups were used. The absolute configuration (SS,SFc,S) has been determined by single-crystal X-ray analysis and chemical correlation. An unusual pseudocyclic boatlike transition state has been proposed to explain the stereochemical course of this reaction.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thio-organique, UMR CNRS 6507, ENSICAEN, Université de Caen, 14050 Caen, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Grach
authors.forename: Jana Sopkova-de Oliveira
authors.initials: JS
authors.lastname: Santos
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Lohier
authors.forename: Ljubica
authors.initials: L
authors.lastname: Mojovic
authors.forename: Nelly
authors.initials: N
authors.lastname: Plé
authors.forename: Alain
authors.initials: A
authors.lastname: Turck
authors.forename: Vincent
authors.initials: V
authors.lastname: Reboul
authors.forename: Patrick
authors.initials: P
authors.lastname: Metzner
mesh_terms: D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D005296:Ferrous Compounds; D007097:Imines; C517322:lithium tert-butylsulfinylferrocene; D008094:Lithium