Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversionCitation formats

  • External authors:
  • Joerg Schrittwieser
  • Bas Groenendaal
  • V Resch
  • Diego Ghislieri
  • S. Wallner
  • E-M. Fischereder
  • E. Fuchs
  • B. Grischek
  • J.H. Sattler
  • P Macheroux
  • Wolfgang Kroutil

Standard

Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion. / Schrittwieser, Joerg; Groenendaal, Bas; Resch, V; Ghislieri, Diego; Wallner, S.; Fischereder, E-M.; Fuchs, E.; Grischek, B.; Sattler, J.H.; Macheroux, P; Turner, Nicholas; Kroutil, Wolfgang.

In: Angewandte Chemie - International Edition, Vol. 53, No. 14, 2014, p. 3731-3734.

Research output: Contribution to journalArticle

Harvard

Schrittwieser, J, Groenendaal, B, Resch, V, Ghislieri, D, Wallner, S, Fischereder, E-M, Fuchs, E, Grischek, B, Sattler, JH, Macheroux, P, Turner, N & Kroutil, W 2014, 'Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion', Angewandte Chemie - International Edition, vol. 53, no. 14, pp. 3731-3734. https://doi.org/10.1002/anie.201400027

APA

Schrittwieser, J., Groenendaal, B., Resch, V., Ghislieri, D., Wallner, S., Fischereder, E-M., ... 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

Vancouver

Schrittwieser J, Groenendaal B, Resch V, Ghislieri D, Wallner S, Fischereder E-M et al. Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion. Angewandte Chemie - International Edition. 2014;53(14):3731-3734. https://doi.org/10.1002/anie.201400027

Author

Schrittwieser, Joerg ; Groenendaal, Bas ; Resch, V ; Ghislieri, Diego ; Wallner, S. ; Fischereder, E-M. ; Fuchs, E. ; Grischek, B. ; Sattler, J.H. ; Macheroux, P ; Turner, Nicholas ; Kroutil, Wolfgang. / Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 14. pp. 3731-3734.

Bibtex

@article{bbccfac0179e46769d97ad0783d4ebf4,
title = "Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion",
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",
volume = "53",
pages = "3731--3734",
journal = "Angewandte Chemie, International Edition",
issn = "1433-7851",
publisher = "John Wiley & Sons Ltd",
number = "14",

}

RIS

TY - JOUR

T1 - Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion

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

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

VL - 53

SP - 3731

EP - 3734

JO - Angewandte Chemie, International Edition

JF - Angewandte Chemie, International Edition

SN - 1433-7851

IS - 14

ER -