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Versatile Access to Chiral Indolines by Catalytic Asymmetric Fischer Indolization

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Martínez,  Alberto
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Webber,  Matthew J.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Müller,  Steffen
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Martínez, A., Webber, M. J., Müller, S., & List, B. (2013). Versatile Access to Chiral Indolines by Catalytic Asymmetric Fischer Indolization. Angewandte Chemie International Edition, 52(36), 9486-9490. doi:10.1002/anie.201301618.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-C9F6-4
Abstract
“Fisching” for complexity: The chiral Brønsted acid (R)‐STRIP catalyzes the asymmetric Fischer indolization of a range of monosubstituted cyclopentanones and cyclohexanones to give chiral fused indolines bearing a quaternary stereogenic center at the 3‐position. The method has been extended to include substrates bearing a tethered nucleophile, thus allowing for enantioselective indolization/ring‐closing cascades to complex propellanes featuring two vicinal quaternary stereocenters.