Open AccessAsymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
Author(s) -
Wolfgang Kroutil,
EvaMaria Fischereder,
Christine Fuchs,
Horst Lechner,
Francesco G. Mutti,
Desiree Pressnitz,
Aashrita Rajagopalan,
Johann H. Sattler,
Robert C. Simon,
Elina Siirola
Publication year - 2013
Publication title -
organic process research and development
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.904
H-Index - 109
eISSN - 1520-586X
pISSN - 1083-6160
DOI - 10.1021/op4000237
Subject(s) - primary (astronomy) , kinetic resolution , chemistry , enantioselective synthesis , regioselectivity , ring (chemistry) , enantiomeric excess , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , physics , astronomy
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.