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@ARTICLE{Klein:902536,
author = {Klein, Andreas and Albrecht, Anna Christina and Pietruszka,
Jörg},
title = {{C}hemoenzymatic {O}ne-{P}ot {P}rocess for the {S}ynthesis
of {T}etrahydroisoquinolines},
journal = {Catalysts},
volume = {11},
number = {11},
issn = {2073-4344},
address = {Basel},
publisher = {MDPI},
reportid = {FZJ-2021-04338},
pages = {1389 -},
year = {2021},
abstract = {1,2,3,4‑Tetrahydyroisoquinolines form a valuable scaffold
for a variety of bioactive secondary metabolites and
commercial pharmaceuticals. Due to the harsh or complex
conditions of the conventional chemical synthesis of this
molecular motif, alternative mild reaction pathways are in
demand. Here we present an easy-to-operate chemoenzymatic
one-pot process for the synthesis of tetrahydroisoquinolines
starting from benzylic alcohols and an amino alcohol. We
initially demonstrate the oxidation of 12 benzylic alcohols
by a laccase/TEMPO system to the corresponding aldehydes,
which are subsequently integrated in a phosphate salt
mediated Pictet–Spengler reaction with m‑tyramine. The
reaction conditions of both individual reactions were
analyzed separately, adapted to each other, and a
straightforward one-pot process was developed. This enables
the production of 12 1,2,3,4‑tetrahydyroisoquinolines with
yields of up to $87\%$ with constant reaction conditions in
phosphate buffer and common laboratory glass bottles without
the supplementation of any additives.},
cin = {IBG-1 / IBOC},
ddc = {540},
cid = {I:(DE-Juel1)IBG-1-20101118 / I:(DE-Juel1)IBOC-20090406},
pnm = {2171 - Biological and environmental resources for
sustainable use (POF4-217)},
pid = {G:(DE-HGF)POF4-2171},
typ = {PUB:(DE-HGF)16},
UT = {WOS:000725862600001},
doi = {10.3390/catal11111389},
url = {https://juser.fz-juelich.de/record/902536},
}