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Issue 92, 2018
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Biocompatible metal-assisted C–C cross-coupling combined with biocatalytic chiral reductions in a concurrent tandem cascade

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Abstract

In this study, we present a concurrent chemo/biocatalytic one pot reaction cascade by combining a metal (Pd/Cu) assisted Liebeskind–Srogl (L–S) coupling with an enantioselective enzymatic reduction for the production of chiral amines and alcohols. The latter transformation was realized by applying enantiocomplementary alcohol dehydrogenases from Lactobacillus kefir (R-selective) and Rhodococcus ruber (S-selective). Compatibility issues were solved by investigating first the L–S-coupling protocol in water at room temperature. Subsequently, we investigated two different biphasic systems and applied a biomimicking approach to separate enzyme-deactivating components. By using a lipophilic membrane in a smart reactor design, we were able to perform concurrent catalytic cascades with overall concentrations up to 100 mM substrate and to produce 1-phenylethylamine and several chiral alcohols in high yields (up to 81% over 2 steps) and enantiomeric purity ((+) and (−)-enantiomers both with 99% ee).

Graphical abstract: Biocompatible metal-assisted C–C cross-coupling combined with biocatalytic chiral reductions in a concurrent tandem cascade

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Publication details

The article was received on 09 Jul 2018, accepted on 16 Oct 2018 and first published on 01 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC05304A
Citation: Chem. Commun., 2018,54, 12978-12981

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    Biocompatible metal-assisted C–C cross-coupling combined with biocatalytic chiral reductions in a concurrent tandem cascade

    P. Schaaf, T. Bayer, M. Koley, M. Schnürch, U. T. Bornscheuer, F. Rudroff and M. D. Mihovilovic, Chem. Commun., 2018, 54, 12978
    DOI: 10.1039/C8CC05304A

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