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

Das, Sayantani; Majumdar, Nilanjana; De, Chandra Kanta; Kundu, Dipti Sankar; Döhring, Arno; Garczynski, Anika; List, Benjamin

doi:10.1021/jacs.6b12176

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

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

/persons/resource/persons203511

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

/persons/resource/persons132969

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

/persons/resource/persons58516

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

/persons/resource/persons203513

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

/persons/resource/persons58764

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

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Citation

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.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-A18F-6

Abstract

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.