Chemoenzymatic Cascades Combining Biocatalysis and Transition Metal Catalysis for Asymmetric Synthesis
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(18)
Published: Feb. 6, 2023
Abstract
The
combination
of
catalytic
methods
provides
multiple
advantages
in
organic
synthesis,
allowing
access
to
diverse
molecules
a
straightforward
manner.
Merging
metal
and
enzyme
catalysis
is
currently
receiving
great
attention
due
the
possibility
assemble
C−C
coupling,
olefin
metathesis,
hydration
other
reactions
with
exquisite
stereospecificity
displayed
by
enzymes.
Thus,
this
minireview
organized
based
on
action
species
(Pd,
Ru,
Au,
Ir,
Fe…)
different
Special
will
be
paid
design
sequential
processes
concurrent
cascades,
presenting
solutions
such
as
use
surfactants
or
compartmentalization
strategies
for
those
cases
where
incompatibilities
could
hamper
overall
process.
Language: Английский
Chemoenzymatic Cascades Combining Biocatalysis and Transition Metal Catalysis for Asymmetric Synthesis
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(18)
Published: Feb. 6, 2023
Abstract
The
combination
of
catalytic
methods
provides
multiple
advantages
in
organic
synthesis,
allowing
access
to
diverse
molecules
a
straightforward
manner.
Merging
metal
and
enzyme
catalysis
is
currently
receiving
great
attention
due
the
possibility
assemble
C−C
coupling,
olefin
metathesis,
hydration
other
reactions
with
exquisite
stereospecificity
displayed
by
enzymes.
Thus,
this
minireview
organized
based
on
action
species
(Pd,
Ru,
Au,
Ir,
Fe…)
different
Special
will
be
paid
design
sequential
processes
concurrent
cascades,
presenting
solutions
such
as
use
surfactants
or
compartmentalization
strategies
for
those
cases
where
incompatibilities
could
hamper
overall
process.
Language: Английский
Merging Gold(I) Catalysis with Amine Transaminases in Cascade Catalysis: Chemoenzymatic Transformation of Propargylic Alcohols into Enantioenriched Allylic Amines
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(22), P. 3856 - 3866
Published: Oct. 3, 2022
Abstract
The
compatibility
between
gold(I)
catalysts
and
amine
transaminases
has
been
explored
to
transform
racemic
propargylic
alcohols
into
enantioenriched
allylic
amines
in
a
straightforward
selective
manner.
synthetic
approach
consists
of
gold(I)‐catalysed
Meyer‐Schuster
rearrangement
series
2‐arylpent‐3‐yn‐2‐ols
subsequent
stereoselective
enzyme‐catalysed
transamination
the
resulting
α,β‐unsaturated
prochiral
ketones.
design
cascade
processes
involving
sequential
or
concurrent
approaches
studied
our
search
for
ideal
reaction
conditions
produce
desired
amines.
Thus,
N‐heterocyclic
carbene
complex
[1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]‐[bis(trifluoromethanesulfonyl)‐imide]gold(I)
([Au(IPr)(NTf
2
)]
(
A
)
aqueous
medium
was
found
be
an
catalyst,
while
selective,
made‐in‐house
commercial
permitted
asymmetric
synthesis
both
E
)‐4‐arylpent‐3‐en‐2‐amine
enantiomers
good
isolated
yields
(53–84%)
excellent
stereoselectivities
(97
>99%
enantiomeric
excess).
magnified
image
Language: Английский
Gold and Biocatalysis for the Stereodivergent Synthesis of Nor(pseudo)ephedrine Derivatives: Cascade Design Toward Amino Alcohols, Diols, and Diamines
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(7), P. 1036 - 1047
Published: March 2, 2023
Abstract
The
combination
of
gold(I)
and
enzyme
catalysis
has
provided
access
to
a
series
nor(pseudo)ephedrine
derivatives
in
regio‐
stereoselective
manner.
approach
involves
developing
IPrAuNTf
2
‐catalyzed
hydration
1‐phenylprop‐2‐yn‐1‐yl
acetate
or
N
‐(1‐phenylprop‐2‐yn‐1‐yl)acetamide,
followed
by
(dynamic)
asymmetric
biotransamination
bioreduction
the
corresponding
keto
ester
amide
intermediates.
Enzyme
actions
were
completely
selective
towards
modification
methyl
ketones
highly
manner,
allowing
synthesis
enantio‐
diastereomerically
enriched
products
using
either
racemic
optically
active
starting
materials.
Thus,
amino
alcohol,
diol,
diamine
produced
from
propargyl
esters
amides
(57
86%
isolated
yield),
biocatalyst
choice
determining
(stereo)selectivity
overall
cascade
process
(70–99%
diastereomeric
excess
>98%
enantiomeric
excess),
providing
compounds
straightforward
magnified
image
Language: Английский
β,β‐Disubstituted Alkan‐2‐ones from Propargylic Alcohols Combining a Meyer‐Schuster Rearrangement and Asymmetric Alkene Bioreduction
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(22), P. 4737 - 4746
Published: Aug. 14, 2024
Abstract
The
combination
of
a
gold(I)
N‐heterocyclic
carbene
complex
and
an
ene‐reductase
(ERED)
has
made
possible
the
synthesis
enantiopure
β,β‐disubstituted
ketones
in
one‐pot
concurrent
approach.
protocol
consists
Meyer‐Schuster
rearrangement
racemic
propargylic
tertiary
alcohols
using
[1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]‐[bis(trifluoromethanesulfonyl)‐imide]gold(I)
(IPrAuNTf
2
),
followed
by
asymmetric
alkene
reduction
α,β‐unsaturated
ketone
intermediate
Zymomonas
mobilis
ERED
(NCR‐ERED).
chemoenzymatic
cascade
was
optimised
with
model
substrate,
where
E
/
Z
‐isomers
both
generated
(
R
)‐ketone,
which
rationalised
silico
molecular
docking
experiments.
then
applied
towards
production
series
)‐4‐substituted‐alkan‐2‐ones
form
straightforward
manner.
Language: Английский