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

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...

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Veröffentlicht in:Angewandte Chemie 2021-04, Vol.133 (16), p.8799-8803
Hauptverfasser: Yao, Peiyuan, Marshall, James R., Xu, Zefei, Lim, Jesmine, Charnock, Simon J., Zhu, Dunming, Turner, Nicholas J.
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Sprache:eng
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Zusammenfassung: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 >20 different preparative scale transformations were performed highlighting the scalability of this system. The asymmetric synthesis of N‐substituted α‐amino esters has been achieved, in high yields and excellent enantioselectivities, employing sequence diverse metagenomic imine reductases (IREDs).
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202016589