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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

Contributor(s):
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
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Further Information

Publication History

Publication Date:
17 March 2017 (online)

 
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Key words

phosphoric acid - kinetic resolution - amines - asymmetric catalysis - condensation

Significance

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.


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Comment

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.


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