title: Synthesis of optically pure vic-sulfanyl amines mediated by a remote sulfinyl group.
abstract: Enantiomerically pure syn-1,2-diaryl-1,2-sulfanylamine derivatives can be obtained in a completely stereoselective manner by reaction of the benzylcarbanion Li-(S)-1 with N-phenyl (or PMP)-arylidene aldimines and further desulfinylation with t-BuLi. Theoretical studies at the DFT (mPW1PW91) level with the CPCM model, by using the Gaussian09 program, provide a good explanation for the stereochemical results.
authors.affiliation: Departamento de Química Orgánica (EII), Universidad de Valladolid, Po del Cauce 59, 47011 Valladolid, Spain. yarroyo@eis.uva.es
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Arroyo
authors.forename: M Ascensión
authors.initials: MA
authors.lastname: Sanz-Tejedor
authors.forename: Inés
authors.initials: I
authors.lastname: Alonso
authors.forename: José L
authors.initials: JL
authors.lastname: García-Ruano
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D013438:Sulfhydryl Compounds