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Asymmetric Reductive Amination of Ketones Catalyzed by Imine Reductases
Author(s) -
Wetzl Dennis,
Gand Martin,
Ross Alfred,
Müller Hubertus,
Matzel Philipp,
Hanlon Steven P.,
Müller Michael,
Wirz Beat,
Höhne Matthias,
Iding Hans
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600384
Subject(s) - imine , biocatalysis , chemistry , methylamine , stereoselectivity , reductive amination , catalysis , amination , butylamine , organic chemistry , combinatorial chemistry , ammonia , amine gas treating , reaction mechanism
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.