Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion

Joerg Schrittwieser; Bas Groenendaal; V Resch; Diego Ghislieri; S. Wallner; E-M. Fischereder; E. Fuchs; B. Grischek; J.H. Sattler; P Macheroux; Nicholas Turner; Wolfgang Kroutil

doi:10.1002/anie.201400027

Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion

Joerg Schrittwieser
, Bas Groenendaal
, V Resch
, Diego Ghislieri
, S. Wallner
, E-M. Fischereder
, E. Fuchs
, B. Grischek
, J.H. Sattler
, P Macheroux
, Nicholas Turner
, Wolfgang Kroutil

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	3731-3734
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	14
DOIs	https://doi.org/10.1002/anie.201400027
Publication status	Published - 2014

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10.1002/anie.201400027

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Schrittwieser, J., Groenendaal, B., Resch, V., Ghislieri, D., Wallner, S., Fischereder, E.-M., Fuchs, E., Grischek, B., Sattler, J. H., Macheroux, P., Turner, N., & Kroutil, W. (2014). Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion. Angewandte Chemie - International Edition, 53(14), 3731-3734. https://doi.org/10.1002/anie.201400027

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abstract = "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.",

author = "Joerg Schrittwieser and Bas Groenendaal and V Resch and Diego Ghislieri and S. Wallner and E-M. Fischereder and E. Fuchs and B. Grischek and J.H. Sattler and P Macheroux and Nicholas Turner and Wolfgang Kroutil",

year = "2014",

doi = "10.1002/anie.201400027",

language = "English",

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AU - Schrittwieser, Joerg

AU - Groenendaal, Bas

AU - Resch, V

AU - Ghislieri, Diego

AU - Wallner, S.

AU - Fischereder, E-M.

AU - Fuchs, E.

AU - Grischek, B.

AU - Sattler, J.H.

AU - Macheroux, P

AU - Turner, Nicholas

AU - Kroutil, Wolfgang

PY - 2014

Y1 - 2014

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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

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion

Abstract

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