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Deracemization By Simultaneous Bio‐oxidative Kinetic Resolution and Stereoinversion
Author(s) -
Schrittwieser Joerg H.,
Groenendaal Bas,
Resch Verena,
Ghislieri Diego,
Wallner Silvia,
Fischereder EvaMaria,
Fuchs Elisabeth,
Grischek Barbara,
Sattler Johann H.,
Macheroux Peter,
Turner Nicholas J.,
Kroutil Wolfgang
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400027
Subject(s) - kinetic resolution , chemistry , enantioselective synthesis , enantiomer , enantiomeric excess , combinatorial chemistry , stereoselectivity , transformation (genetics) , biocatalysis , stereochemistry , yield (engineering) , oxidative phosphorylation , cascade , organic chemistry , catalysis , biochemistry , reaction mechanism , materials science , chromatography , metallurgy , gene
Deracemization, that is, the transformation of a racemate into a single product enantiomer with theoretically 100 % conversion and 100 % ee , is an appealing but also challenging option for asymmetric synthesis. Herein a novel chemo‐enzymatic deracemization concept by a cascade is described: the pathway involves two enantioselective oxidation steps and one non‐stereoselective reduction step, enabling stereoinversion and a simultaneous kinetic resolution. The concept was exemplified for the transformation of rac ‐benzylisoquinolines to optically pure ( S )‐berbines. The racemic substrates were transformed to optically pure products ( ee >97 %) with up to 98 % conversion and up to 88 % yield of isolated product.
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