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

Journal Article (2022)
Authors

Lukas Schober (Bielefeld University)

F. Tonin (TU Delft - BT/Biocatalysis)

Ulf Hanefeld (TU Delft - BT/Biocatalysis)

Harald Gröger (Bielefeld University)

Research Group
BT/Biocatalysis
Copyright
© 2022 Lukas Schober, F. Tonin, U. Hanefeld, Harald Gröger
To reference this document use:
https://doi.org/10.1002/ejoc.202101035
More Info
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Publication Year
2022
Language
English
Copyright
© 2022 Lukas Schober, F. Tonin, U. Hanefeld, Harald Gröger
Research Group
BT/Biocatalysis
Issue number
7
Volume number
2022
DOI:
https://doi.org/10.1002/ejoc.202101035
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Abstract

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 multi-step 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 chemocatalysis, biocatalysis and flow chemistry.