title: Asymmetric synthesis of alpha-branched allylic amines by the Rh(I)-catalyzed addition of alkenyltrifluoroborates to N-tert-butanesulfinyl aldimines.
abstract: The first Rh(I)-catalyzed addition of alkenylboron reagents to imines is described. The Rh(I)-catalyzed addition of potassium alkenyltrifluoroborate salts to both aromatic and aliphatic N-tert-butanesulfinyl aldimines proceeds in good yields (up to 97%) and with very high diastereoselectivities (95:5 to >99:1). This new method enables the general and efficient asymmetric synthesis of the important class of alpha-branched allylic amines from readily available and stable starting materials.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Katrien
authors.initials: K
authors.lastname: Brak
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D000588:Amines / Q000138:chemical synthesis*; D001881:Borates; D002384:Catalysis; D007097:Imines; D012238:Rhodium
chemical_list: D000588:Amines; D001881:Borates; D007097:Imines; D012238:Rhodium