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Asymmetric Reductive Amination of Ketones Catalyzed by Imine Reductases

2016; Wiley; Volume: 8; Issue: 12 Linguagem: Inglês

10.1002/cctc.201600384

1867-3899

Dennis Wetzl, Martin Gand, Alfred Ross, Hubertus Müller, Philipp Matzel, Steven P. Hanlon, Michael Müller, Beat Wirz, Matthias Höhne, Hans Iding,

Biochemical and Molecular Research

Abstract Biocatalysis employing imine reductases is a promising approach for the one‐step generation of chiral amines from ketones. The enzymes reported for this process suffer from low activity and moderate stereoselectivity. We identified a set of enzymes that facilitate this reaction with high to quantitative conversions from a library of 28 imine reductases. This enabled the conversion of ketones with ammonia, methylamine, or butylamine into the corresponding amines. Most importantly, we performed preparative (>100 mg) scale syntheses of amines such as (1 S ,3 R )‐ N ,3‐dimethylcyclohexylamine and ( R )‐ N ‐methyl‐2‐aminohexane with excellent stereochemical purities (98 % de , 96 % ee ) in good yields.