title: Intermolecular alkyl radical additions to enantiopure N-tert-butanesulfinyl aldimines.
abstract: The sulfinyl group in (R)-N-tert-butanesulfinyl aldimines provides efficient control of the stereoselectivity in the intermolecular reactions with alkyl radicals. The methodology is applicable to aryl, heteroaryl, benzyl, and alkynyl imines, even those containing CN, CO2Me, COR, and OH groups. The best results are attained with hindered radicals (tertiary and secondary ones) without C═N bond reduction. This reaction complements the well-established organometallic additions to N-sulfinyl aldimines to obtain enantiomerically pure functionalized α-branched primary amines.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049-Cantoblanco, Madrid, Spain.
authors.forename: José A
authors.initials: JA
authors.lastname: Fernández-Salas
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Maestro
authors.forename: M Mercedes
authors.initials: MM
authors.lastname: Rodríguez-Fernández
authors.forename: José L
authors.initials: JL
authors.lastname: García-Ruano
authors.forename: Inés
authors.initials: I
authors.lastname: Alonso
mesh_terms: D000473:Alkanes / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000473:Alkanes; D000588:Amines; D007097:Imines; D013452:Sulfonium Compounds