Bridging between Organocatalysis and Biocatalysis: Asymmetric Addition of Acetaldehyde to β‐Nitrostyrenes Catalyzed by a Promiscuous Proline‐Based Tautomerase

Abstract

Nichtnatürliche Schönheit: Das Enzym 4-Oxalocrotonat-Tautomerase (4-OT) zeigt eine nichtnatürliche Aktivität, indem es eine Michael-Addition von Acetaldehyd an Nitrostyrol katalysiert. Die Reaktion verläuft wahrscheinlich über die Bildung eines Enamins zwischen dem N-terminalen Prolin von 4-OT und Acetaldehyd in Anlehnung an organokatalysierte Reaktionen. Eine hohe Stereoselektivität, geringe Katalysatormengen und Durchführbarkeit in Wasser zeichnen die Methode aus. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.