Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses

Schober L, Tonin F, Hanefeld U, Gröger H (2022)
European Journal of Organic Chemistry (7): e202101035.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Schober, LukasUniBi; Tonin, Fabio; Hanefeld, Ulf; Gröger, HaraldUniBi
Abstract / Bemerkung
A sequential-type as well as a tandem-type chemoenzymatic flow cascade combining an organocatalytic aldol reaction and a biocatalytic reduction to form stereoselectively a 1,3-diol with two stereogenic centers were developed. Initially, a comprehensive screening of 24 alcohol dehydrogenases was carried out and the identified candidates were applied in different multistep flow cascades. All four stereoisomers of the desired 1,3-diol product are accessible via a sequential flow approach with product formation-related conversions of up to 76% over two steps, isolated yields of up to 64% and enantiomeric excess of >99% in all cases. In addition, a tandem-type flow process, performing both reaction steps simultaneously, was established leading to 51 % conversion with >99% ee and 8:1 d.r. and representing a combination of the fields of asymmetric chemo-catalysis, biocatalysis and flow chemistry.
Stichworte
Asymmetric catalysis; Biocatalysis; Chemoenzymatic cascades; Flow; chemistry; Organocatalysis
Erscheinungsjahr
2022
Zeitschriftentitel
European Journal of Organic Chemistry
Ausgabe
7
Art.-Nr.
e202101035
ISSN
1434-193X
eISSN
1099-0690
Page URI
https://pub.uni-bielefeld.de/record/2962202

Zitieren

Schober L, Tonin F, Hanefeld U, Gröger H. Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses. European Journal of Organic Chemistry . 2022;(7): e202101035.
Schober, L., Tonin, F., Hanefeld, U., & Gröger, H. (2022). Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses. European Journal of Organic Chemistry (7), e202101035. https://doi.org/10.1002/ejoc.202101035
Schober, L., Tonin, F., Hanefeld, U., and Gröger, H. (2022). Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses. European Journal of Organic Chemistry :e202101035.
Schober, L., et al., 2022. Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses. European Journal of Organic Chemistry , (7): e202101035.
L. Schober, et al., “Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses”, European Journal of Organic Chemistry , 2022, : e202101035.
Schober, L., Tonin, F., Hanefeld, U., Gröger, H.: Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses. European Journal of Organic Chemistry . : e202101035 (2022).
Schober, Lukas, Tonin, Fabio, Hanefeld, Ulf, and Gröger, Harald. “Combination of Asymmetric Organo- and Biocatalysis in Flow Processes and Comparison with their Analogous Batch Syntheses”. European Journal of Organic Chemistry 7 (2022): e202101035.

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