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

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...

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Veröffentlicht in:Organic process research & development 2013-05, Vol.17 (5), p.751-759
Hauptverfasser: Kroutil, Wolfgang, Fischereder, Eva-Maria, Fuchs, Christine S, Lechner, Horst, Mutti, Francesco G, Pressnitz, Desiree, Rajagopalan, Aashrita, Sattler, Johann H, Simon, Robert C, Siirola, Elina
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Sprache:eng
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Zusammenfassung: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/op4000237