Synfacts 2017; 13(04): 0419
DOI: 10.1055/s-0036-1590094
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Kinetic Resolution of Primary Amines through Chiral Phosphoric Acid Catalysis

Benjamin List
Nobuya Tsuji
Das S. * Majumdar N. * De CK. * Kundu DS. * Döhring A. * Garczynski A. * List B. * Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines.

J. Am. Chem. Soc. 2017;
139: 1357-1359
Further Information

Publication History

Publication Date:
17 March 2017 (online)



The List group reports a kinetic resolution of primary amines by selective condensation with a 1,3-diketone. The reaction is catalyzed by a chiral BINOL-derived phosphoric acid. The method is applicable to both benzylamine derivatives and aliphatic substrates.



The authors demonstrated an acid-catalyzed enantioselective carbonyl–amine condensation through a kinetic resolution of primary amines. There is great potential of the observed reactivity in many other transformations.