Recent Advances in Palladium-Catalyzed Enantioselective Cyclization for the Construction of Atropisomers
Catalysts,
Год журнала:
2025,
Номер
15(4), С. 320 - 320
Опубликована: Март 27, 2025
Axially
chiral
structures
have
become
increasingly
common
in
modern
materials
and
pharmaceuticals,
especially
as
ligands
organocatalysts,
highlighting
their
growing
significance.
In
the
field
of
pharmaceutical
research,
there
are
several
notable
examples
worth
highlighting,
such
antibiotics
vancomycin,
Knipholone,
Mastigophorene
A.
Over
past
decade,
availability
axially
compounds
has
significantly
improved
through
advancements
existing
strategies
introduction
catalytic
atroposelective
synthesis
concepts.
These
synthetic
not
only
broaden
scope
chemical
reactions,
but
also
facilitate
construction
frameworks
with
high
application
value.
Currently,
various
methods
available
for
achieving
stereoselective
under
catalyst
control,
including
desymmetrization,
(dynamic)
kinetic
resolution,
cross-coupling
de
novo
ring-forming
synthesis.
This
paper
focuses
on
recent
advances
constructing
atropisomers
palladium-catalyzed
asymmetric
cyclization
strategies.
Язык: Английский
Recent advances in the catalytic asymmetric construction of axially chiral azole-based frameworks
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(23), С. 6819 - 6849
Опубликована: Янв. 1, 2024
This
review
highlights
recent
advances
in
the
atroposelective
preparation
of
axially
chiral
azole
derivatives,
emphasizing
mechanistic
insights
and
synthetic
applications
development
this
class
five-membered
heterocyclic
frameworks.
Язык: Английский
Manganese-Catalyzed Asymmetric Hydrogenation for Atroposelective Dynamic Kinetic Resolution of Heterobiaryl Ketone N-Oxides
ACS Catalysis,
Год журнала:
2024,
Номер
unknown, С. 17633 - 17641
Опубликована: Ноя. 15, 2024
An
atroposelective
dynamic
kinetic
resolution
of
configurationally
labile
heterobiaryl
ketone
N-oxides
via
Mn-catalyzed
asymmetric
hydrogenation
has
been
disclosed.
By
use
a
structurally
finely
tuned
chiral
ferrocenyl
P,N,N-ligand,
the
proceeds
smoothly
under
mild
conditions
with
simultaneous
installation
central
and
axial
chirality,
giving
wide
range
atropisomeric
1-arylisoquinoline
2-arylpyridine
bearing
alcohol
structure
high
diastereo-
enantioselectivities.
The
diastereomer
product
could
be
readily
prepared
in
stereospecific
way
complete
inversion
chirality
Mitsunobu
reaction.
value
this
central-
axial-chiral
N-oxide
scaffold
is
preliminarily
demonstrated
by
its
successful
utility
as
catalyst
allylation
benzaldehyde
allyltrichlorosilane.
Язык: Английский
Symmetric Anion Mediated Dynamic Kinetic Asymmetric Knoevenagel Reaction for N−C and N−N Atropisomers Synthesis
Hongyu Qu,
Chenyang Huo,
Jimeng Ge
и другие.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Авг. 21, 2024
A
symmetric
anion
mediated
dynamic
kinetic
asymmetric
Knoevenagel
reaction
was
established
as
a
general
and
efficient
method
for
accessing
both
N-C
N-N
atropisomers.
The
resulting
highly
enantio-pure
pyridine-2,6(1H,3H)-diones
exhibit
diverse
structures
functional
groups.
key
to
excellent
regio-
remote
enantiocontrol
could
be
owed
the
hydrogen
bond
between
enolate
triflamide
block
of
organocatalyst.
This
connected
iminium
cation
by
chiral
backbone.
mechanism
investigation
via
control
experiments,
correlation
analysis,
density
theory
calculations
further
revealed
how
stereochemical
information
transferred
from
catalyst
into
axially
pyridine-2,6(1H,3H)-diones.
synthetic
applications
also
demonstrated
reaction's
potential.
Язык: Английский
Symmetric Anion Mediated Dynamic Kinetic Asymmetric Knoevenagel Reaction for N−C and N−N Atropisomers Synthesis
Hongyu Qu,
Chenyang Huo,
Jimeng Ge
и другие.
Angewandte Chemie,
Год журнала:
2024,
Номер
136(39)
Опубликована: Июль 3, 2024
Abstract
A
symmetric
anion
mediated
dynamic
kinetic
asymmetric
Knoevenagel
reaction
was
established
as
a
general
and
efficient
method
for
accessing
both
N−C
N−N
atropisomers.
The
resulting
highly
enantio‐pure
pyridine‐2,6(1
H
,3
)‐diones
exhibit
diverse
structures
functional
groups.
key
to
excellent
regio‐
remote
enantiocontrol
could
be
owed
the
hydrogen
bond
between
enolate
triflamide
block
of
organocatalyst.
This
connected
iminium
cation
by
chiral
backbone.
mechanism
investigation
via
control
experiments,
correlation
analysis,
density
theory
calculations
further
revealed
how
stereochemical
information
transferred
from
catalyst
into
axially
)‐diones.
synthetic
applications
also
demonstrated
reaction's
potential.
Язык: Английский
DFT-Assisted Atroposelective Construction of Indole-Fused N-Heteroaromatic Frameworks through Palladium-Catalyzed C–H Imidoylation
ACS Catalysis,
Год журнала:
2024,
Номер
15(1), С. 201 - 210
Опубликована: Дек. 16, 2024
On
the
basis
of
density
functional
theory
(DFT)
calculations,
we
designed
an
asymmetric
synthesis
method
for
axially
chiral
biaryls
through
C(sp2)–H
imidoylative
cyclization
isocyanides.
Building
on
this,
successfully
synthesized
compounds
containing
indole-fused
N-heteroaromatic
frameworks
via
palladium-catalyzed
C–H
imidoylation
to
achieve
high
yields
and
enantioselectivity.
Various
efficient
pathways
facilitated
ring
derivatives
with
either
C–C
or
C–N
axial
chirality.
This
not
only
provides
diverse
strategy
but
also
demonstrates
that
DFT-assisted
design
is
a
reliable
tool
accurately
predicting
reaction
stereoselectivity
effectively
reducing
workload
chemical
experiments.
Язык: Английский