Asymmetric Preparation of <i>prim</i>-, <i>sec</i>-, and <i>tert</i>-Amines Employing Selected Biocatalysts

Wolfgang Kroutil, Eva‐Maria Fischereder, Christine Fuchs, Horst Lechner, Francesco G. Mutti, Desiree Pressnitz, Aashrita Rajagopalan, Johann H. Sattler, Robert C. Simon, Elina Siirola

Organic Process Research & Development · 2013 · 122 citations · 102 references

Concepts

Abstract

High Resolution Image Download MS PowerPoint Slide This account focuses on the application of ω-transaminases, lyases, and oxidases for the preparation of amines considering mainly work from our own lab. Examples are given to access α-chiral primary amines from the corresponding ketones as well as terminal amines from primary alcohols via a two-step biocascade. 2,6-Disubstituted piperidines, as examples for secondary amines, are prepared by biocatalytical regioselective asymmetric monoamination of designated diketones followed by spontaneous ring closure and a subsequent diastereoselective reduction step. Optically pure tert -amines such as berbines and N -methyl benzylisoquinolines are obtained by kinetic resolution via an enantioselective aerobic oxidative C–C bond formation.

References

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