[Zurück]

P. Schaaf, T. Bayer, M. Koley, M. Schnürch, U. Bornscheuer, F. Rudroff, M.D. Mihovilovic:
"Biocompatible metal-assisted C-C cross-coupling combined with biocatalytic chiral reductions in a concurrent tandem cascade";
Chemical Communications, 54 (2018), S. 12978 - 12981.

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).

http://dx.doi.org/10.1039/c8cc05304a