Benjamin W Turnpenny1, Sherry R Chemler1. 1. Department of Chemistry, Natural Science Complex, The State University of New York at Buffalo, Buffalo, NY 14260, USA.
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.
Chiral vicinal diamines, including n class="Chemical">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: Caren Röben; José A Souto; Yolanda González; Anton Lishchynskyi; Kilian Muñiz Journal: Angew Chem Int Ed Engl Date: 2011-08-30 Impact factor: 15.336
Authors: Shuklendu D Karyakarte; Fatima C Sequeira; Garrick H Zibreg; Guoqing Huang; Josiah P Matthew; Marina M M Ferreira; Sherry R Chemler Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415