Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(62)
Published: Aug. 7, 2023
Axially
chiral
compounds
are
attracting
more
attention
recently.
Although
hydrogen
bonds
reported
as
a
vital
weak
force
that
influences
the
properties
of
compounds,
effect
intramolecular
on
atropisomerization
Caryl
-Caryl
single
has
not
yet
been
well
quantitatively
investigated.
Here,
series
axially
biaryl
were
synthesized
to
study
rotational
barriers
C-C
axis.
Experimental
studies
demonstrated
barrier
bonding
9
was
significantly
lower
(46.7
kJ
mol-1
)
than
10
without
bonds.
Furthermore,
theoretical
revealed
bond
stabilized
transition
state
(TS)
tri-ortho-substituted
9,
relieving
steric
repulsion
in
TS.
We
believe
this
will
provide
chemists
with
deeper
understanding
process
compounds.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 9, 2025
The
chemoenzymatic
dynamic
kinetic
resolution
of
2-(quinolin-8-yl)benzylalcohols
using
a
combination
lipases
and
ruthenium
catalysts
is
described.
While
CalB
lipase
performs
highly
selective
enzymatic
resolution,
the
with
Shvo's
or
Bäckvall's
promotes
atropisomerization
substrate
via
reversible
formation
configurationally
labile
aldehydes,
thereby
enabling
resolution.
This
synergistic
approach
was
applied
to
synthesis
variety
heterobiaryl
acetates
in
excellent
yields
enantioselectivities.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(14), P. 3894 - 3899
Published: Jan. 1, 2024
The
first
organocatalyzed
asymmetric
reductive
amination
towards
axially
chiral
N
-arylindoles
proceeding
through
n
→
π*
interaction-induced
dynamic
kinetic
resolution
is
reported.
ChemCatChem,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 8, 2024
Abstract
Due
to
their
molecular
topology,
atropisomers
serve
as
highly
valuable
chiral
frameworks
for
diverse
applications
across
academic
research
and
industry.
Despite
the
availability
of
numerous
established
catalytic
methods
synthesis,
there
is
still
a
high
demand
development
novel
resourceful
strategies.
In
this
concept
article,
we
will
detail
our
studies
on
use
transient
Lewis
acid‐base
interactions
(LABI)
dynamization
strategy
synthesis
(hetero)biaryl
by
Dynamic
Kinetic
Resolution
(DKR).
The
formation
cyclic
transition
states,
resulting
from
interaction
between
an
acidic
functionality
basic
counterpart,
plays
key
role
in
facilitating
racemization
substantially
reducing
barrier
atropisomerization.
scenario,
have
employed
transformations
aimed
at
neutralizing
nature
acid,
ultimately
leading
configurationally
stable
enantioenriched
compounds.
design
substrates
employment
stereoselective
strategies
based
metal
biocatalysis
resolution
detailed.
Specific
emphasis
preparation
axially
motifs
commonly
found
catalysis
or
medicinal
chemistry
also
be
given.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(37)
Published: June 25, 2024
A
ruthenium-catalyzed
reductive
amination
via
asymmetric
transfer
hydrogenation
(ATH)
has
been
used
to
perform
an
efficient
dynamic
kinetic
resolution
(DKR)
of
N-aryl
2-formyl
pyrroles
decorated
with
a
phosphine
moiety
positioned
at
the
ortho'
position.
The
strategy
relies
on
labilization
stereogenic
axis
in
substrate
facilitated
by
transient
Lewis
acid-base
interaction
(LABI)
between
carbonyl
carbon
and
phosphorus
center.
reaction
features
broad
scope
aliphatic
amines
pyrrole
scaffolds,
proceeds
under
very
mild
conditions
afford
P,N
atropisomers
good
high
yields
excellent
enantioselectivities
(up
99
%
ee)
for
both
diphenyl
dicyclohexylphosphino
derivatives.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
unknown, P. 17633 - 17641
Published: Nov. 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.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
136(3)
Published: Nov. 2, 2023
Abstract
With
the
rapid
development
of
asymmetric
catalysis,
demand
for
enantioselective
synthesis
complex
and
diverse
molecules
with
different
chiral
elements
is
increasing.
Owing
to
unique
features
atropisomerism,
catalytic
atropisomers
has
attracted
a
considerable
interest
from
chemical
science
community.
In
particular,
introducing
additional
elements,
such
as
carbon
centered
chirality,
heteroatomic
planar
helical
into
provides
an
opportunity
incorporate
new
properties
axially
compounds,
thus
expanding
potential
applications
atropisomers.
Thus,
it
important
perform
transformations
synthesize
bearing
multiple
elements.
spite
challenges
in
transformations,
recent
years,
chemists
have
devised
powerful
strategies
under
organocatalysis
or
metal
synthesizing
wide
range
enantioenriched
Therefore,
become
emerging
field.
This
review
summarizes
progress
this
field
indicates
challenges,
thereby
promoting
horizon.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
60(5), P. 582 - 585
Published: Dec. 7, 2023
Quinoline
and
indole
are
important
core
structures
in
biologically
active
compounds
materials.
Atropisomeric
biaryls
consisting
of
quinoline
a
unique
class
axially
chiral
molecules.
We
report
herein
enantioselective
synthesis
3-(
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 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.
