title: Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.
abstract: Chiral vicinal diamines, including 2-aminomethyl indolines and pyrrolidines, are useful as ligands for catalytic asymmetric reactions and are also found as important components of bioactive compounds. Herein is reported the first copper-catalyzed alkene diamination that occurs with high enantioselectivity. The substrate range is the broadest yet reported for this kind of intra-/intermolecular reaction sequence both with respect to γ-alkenyl sulfonamide substrate and external amine nucleophile. The resulting products expand the availability of substituted 2-aminomethyl indolines and pyrrolidines, privileged compounds in asymmetric catalysis and medicinal chemistry. A unique solution to a challenging oxidation problem related to copper catalyst turnover is also presented.
authors.affiliation: Department of Chemistry, Natural Science Complex, The State University of New York at Buffalo, Buffalo, NY 14260, USA.
authors.forename: Benjamin W
authors.initials: BW
authors.lastname: Turnpenny
authors.affiliation: Department of Chemistry, Natural Science Complex, The State University of New York at Buffalo, Buffalo, NY 14260, USA.
authors.forename: Sherry R
authors.initials: SR
authors.lastname: Chemler