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

Schaaf, P and Bayer, T and Koley, M and Schnürch, M and Bornscheuer, UT and Rudroff, F and Mihovilovic, MD (2018) Biocompatible metal-assisted C-C cross-coupling combined with biocatalytic chiral reductions in a concurrent tandem cascade. In: Chemical Communications, 54 (92). pp. 12978-12981.

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Official URL: https://doi.org/10.1039/C8CC05304A


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).

Item Type: Journal Article
Publication: Chemical Communications
Publisher: Royal Society of Chemistry
Additional Information: The copyright for this article belongs to the Authors.
Keywords: alcohol dehydrogenase; alcohol derivative; alpha methylbenzylamine; amine; copper; metal; palladium; water, Article; biocatalysis; chirality; concentration (parameters); cross coupling reaction; enantiomer; enantioselectivity; enzyme inactivation; enzyme substrate; Lactobacillus; Lactobacillus kefir; lipophilicity; nonhuman; one pot synthesis; reduction (chemistry); Rhodococcus ruber; room temperature
Department/Centre: Division of Interdisciplinary Sciences > Centre for Society and Policy (formerly: Centre for Contemporary Studies)
Date Deposited: 02 Sep 2022 04:20
Last Modified: 02 Sep 2022 04:20
URI: https://eprints.iisc.ac.in/id/eprint/76358

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