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Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines.

MPG-Autoren
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Das,  Sayantani
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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De,  Chandra Kanta
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Garczynski,  Anika
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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Zitation

Das, S., Majumdar, N., De, C. K., Kundu, D. S., Döhring, A., Garczynski, A., et al. (2017). Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines. Journal of the American Chemical Society, 139(4), 1357-1359. doi:10.1021/jacs.6b12176.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-002C-A18F-6
Zusammenfassung
A Brønsted acid catalyzed kinetic resolution of primary amines is described that is based on the condensation between an amine and a carbonyl compound. 1,3-Diketones react with racemic α-branched amines to furnish the corresponding enantioenriched enaminone and recovered starting material. Good to excellent enantioselectivity was observed with both aromatic and aliphatic primary amines. This process represents the first small-molecule catalyzed kinetic resolution of aliphatic amines.