Catalysis

Enantioselective synthesis

Enantiomeric excess

Amino acid

Enantiomer

Reaction mechanism

Imine

Biochemistry

Stereoisomerism

Reductive amination

Stereochemistry

Combinatorial chemistry

Organic chemistry

Biocatalysis

Amination

Reductase

Enzyme

Asymmetric hydrogenation

Chemistry

Angewandte Chemie International Edition

N ‐Substituted α‐amino esters are widely used as chiral intermediates in a range of pharmaceuticals. Here we report the enantioselective biocatalyic synthesis of N ‐substituted α‐amino esters through the direct reductive coupling of α‐ketoesters and amines employing sequence diverse metagenomic imine reductases (IREDs). Both enantiomers of N ‐substituted α‐amino esters were obtained with high conversion and excellent enantioselectivity under mild reaction conditions. In addition &gt;20 different preparative scale transformations were performed highlighting the scalability of this system.

Asymmetric Synthesis of <i>N</i>‐Substituted α‐Amino Esters from α‐Ketoesters via Imine Reductase‐Catalyzed Reductive Amination

Asymmetric Synthesis of N‐Substituted α‐Amino Esters from α‐Ketoesters via Imine Reductase‐Catalyzed Reductive Amination