Issue 2, 2017

One-step asymmetric synthesis of (R)- and (S)-rasagiline by reductive amination applying imine reductases

Abstract

Imine reductases (IREDs) show great potential as catalysts for reductive amination of ketones to produce chiral secondary amines. In this work, we explored this potential and synthesized the pharmaceutically relevant (R)-rasagiline in high yields (up to 81%) and good enantiomeric excess (up to 90% ee) from the ketone precursor. This one-step approach in aqueous medium represents the shortest synthesis route from achiral starting materials. Furthermore, we demonstrate for the first time that tertiary amines also can be accessed by this route, which provides new opportunities for eco-friendly enzymatic asymmetric syntheses of these important molecules.

Graphical abstract: One-step asymmetric synthesis of (R)- and (S)-rasagiline by reductive amination applying imine reductases

Supplementary files

Article information

Article type
Communication
Submitted
02 nov 2016
Accepted
16 dec 2016
First published
23 dec 2016

Green Chem., 2017,19, 385-389

One-step asymmetric synthesis of (R)- and (S)-rasagiline by reductive amination applying imine reductases

P. Matzel, M. Gand and M. Höhne, Green Chem., 2017, 19, 385 DOI: 10.1039/C6GC03023H

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