Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes†
Lisa Kötzner
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorDr. Matthew J. Webber
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorDr. Alberto Martínez
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorDr. Claudia De Fusco
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Benjamin List
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)===Search for more papers by this authorLisa Kötzner
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorDr. Matthew J. Webber
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorDr. Alberto Martínez
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorDr. Claudia De Fusco
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Benjamin List
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany)===Search for more papers by this authorWe gratefully acknowledge generous support from the Max Planck Society, the European Research Council (Advanced Grant “High Performance Lewis Acid Organocatalysis, HIPOCAT”), and the Ministero dell′Istruzione, dell′Università e della Ricerca (MIUR) (fellowship for C.D.F.). We also thank the members of our HPLC, NMR, MS, and crystallography departments for their support.
Graphical Abstract
Twisting indoles: A novel chiral Brønsted acid, specifically designed for long-range control on a nanoscale, catalyzes the asymmetric synthesis of azahelicenes through a Fischer indolization. The method has the advantage of starting from simple achiral starting materials, which can be modified by changing the protecting group (R2) or the terminal substituents (R1, R3). The products can be further oxidized to polyaromatic systems.
Abstract
The first asymmetric organocatalytic synthesis of helicenes is reported. A novel SPINOL-derived phosphoric acid, bearing extended π-substituents, catalyzes the asymmetric synthesis of helicenes through an enantioselective Fischer indole reaction. A variety of azahelicenes and diazahelicenes could be obtained with good to excellent yields and enantioselectivities.
Supporting Information
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