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Org Process Res Dev. 2013 May 17;17(5):751-759. Epub 2013 Apr 22.

Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts.

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1
Department of Chemistry, University of Graz , Heinrichstrasse 28, A-8010 Graz, Austria ; ACIB GmbH c/o Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.

Abstract

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.

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