TY - JOUR
T1 - Deracemization by Simultaneous Bio-oxidative Kinetic Resolution and Stereoinversion
AU - Schrittwieser, Jörg H.
AU - Groenendaal, Bas
AU - Resch, Verena
AU - Ghislieri, Diego
AU - Wallner, Silvia
AU - Fischereder, Eva-Maria
AU - Fuchs, Elisabeth
AU - Grischek, Barbara
AU - Sattler, Johann H.
AU - Macheroux, Peter
AU - Turner, Nicholas J.
AU - Kroutil, Wolfgang
PY - 2014
Y1 - 2014
N2 - 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.
AB - 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.
U2 - 10.1002/anie.201400027
DO - 10.1002/anie.201400027
M3 - Article
SN - 1521-3773
VL - 53
SP - 3731
EP - 3734
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 14
ER -