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Deracemization of Racemic Amines to Enantiopure (<i>R</i>)‐ and (<i>S</i>)‐amines by Biocatalytic Cascade Employing ω‐Transaminase and Amine Dehydrogenase
52
Citations
47
References
2019
Year
EngineeringOrganic ChemistryEnzymatic ModificationStereoselective SynthesisAmine DehydrogenaseBiochemistryBiocatalysisDiversity-oriented SynthesisCatalysisNatural Product SynthesisAsymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringNatural SciencesEnzyme CatalysisOne‐pot Deracemization Strategyα‐Chiral AminesRacemic AminesSynthetic Chemistry
Abstract A one‐pot deracemization strategy for α‐chiral amines is reported involving an enantioselective deamination to the corresponding ketone followed by a stereoselective amination by enantiocomplementary biocatalysts. Notably, this cascade employing a ω‐transaminase and amine dehydrogenase enabled the access to both ( R )‐and ( S )‐amine products, just by controlling the directions of the reactions catalyzed by them. A wide range of ( R )‐and ( S )‐amines was obtained with excellent conversions (>80 %) and enantiomeric excess (>99 % ee ). Finally, preparative scale syntheses led to obtain enantiopure ( R )‐ and ( S )‐ 13 with the isolated yields of 53 and 75 %, respectively.
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