Issue 5, 2014

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.

Graphical abstract: Copper-catalyzed alkene diamination: synthesis of chiral 2-aminomethyl indolines and pyrrolidines

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Jan 2014
Accepted
17 Feb 2014
First published
17 Feb 2014

Chem. Sci., 2014,5, 1786-1793

Author version available

Copper-catalyzed alkene diamination: synthesis of chiral 2-aminomethyl indolines and pyrrolidines

B. W. Turnpenny and S. R. Chemler, Chem. Sci., 2014, 5, 1786 DOI: 10.1039/C4SC00237G

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