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

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.

Tuning porosity and activity of microporous polymer network organocatalysts by co-polymerisation.

Microporous polymer networks based on binaphthyl phosphoric acids are suitable heterogeneous asymmetric organocatalysts. Herein we show that the porous characteristics of such networks can be fine-tuned by co-polymerisation. This enables us to investigate the influence of the surface area and porosity in microporous networks on their catalytic performance. In this case, the activity of the polymers in an asymmetric hydrogenation reaction is increased by the use of polymers with higher surface areas.