Kinetic Resolution of Primary Amines through Chiral Phosphoric Acid Catalysis
Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines.
J. Am. Chem. Soc. 2017;
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.