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.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(3)
Published: Nov. 2, 2023
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.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
unknown, P. 1147 - 1157
Published: Jan. 3, 2025
This
study
describes
a
photoredox/cobalt
dual-catalyzed
asymmetric
Grignard-type
addition
reaction,
enabling
the
synthesis
of
axially
chiral
hexatomic
(six–six)
N-heterobiaryls
bearing
extra
secondary
alcohol
unit
via
an
efficient
dynamic
kinetic
transformation
racemic
N-heterobiaryl
triflate
substrates.
The
conversion
facilitated
both
photoredox
and
classical
reductive
reaction
conditions
exhibits
good
functional
group
tolerance,
broad
substrate
scope,
satisfactory
stereoselectivity.
Furthermore,
control
experiments
density
theory
calculations
provide
preliminary
mechanistic
insights.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(18), P. 12134 - 12141
Published: Aug. 30, 2023
A
highly
enantio-
and
diastereoselective
dynamic
kinetic
resolution
(DKR)
of
configurationally
labile
3-aryl
indole-2-carbaldehydes
is
described.
The
DKR
proceeds
via
a
Rh-catalyzed
intermolecular
asymmetric
reductive
aldol
reaction
with
acrylate
esters,
simultaneous
generation
three
stereogenic
elements.
strategy
relies
on
the
labilization
axis
that
takes
place
thanks
to
transient
Lewis
acid-base
interaction
(LABI)
between
formyl
group
thioether
moiety
strategically
located
at
ortho'
position.
atropisomeric
indole
products
present
high
degree
functionalization
can
be
further
converted
series
axially
chiral
derivatives,
thereby
expanding
their
potential
application
in
drug
discovery
catalysis.
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
53(22), P. 11165 - 11206
Published: Jan. 1, 2024
This
review
explores
the
fascinating
world
of
molecules
featuring
multiple
stereogenic
elements,
unraveling
different
strategies
designed
over
years
for
their
enantioselective
synthesis.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(6), P. 1269 - 1284
Published: Jan. 31, 2024
Abstract
Axially
chiral
architectures
exist
widely
in
natural
products,
biologically
relevant
molecules,
ligands
and
catalysts
as
well
functional
materials.
Therefore,
catalytic
asymmetric
synthesis
of
atropisomers
has
become
one
the
most
fast‐growing
fields
community
chemistry
rapid
advances
have
occurred.
Among
different
methods
reported,
organocatalytic
atroposelective
dynamic
kinetic
resolution
(DKR)
involving
ring
manipulations
stands
out
a
cutting‐edge
technology
to
construct
axial
chirality
from
point
atom/step
economy.
In
this
DKR
strategy,
configurational
lability
starting
materials
originates
chirally‐labile
structure
cyclic
substrates/intermediates
or
transient
formation
through
noncovalent
interactions
acyclic
substrates.
The
two
material
are
equilibrium
reaction
medium,
ensuring
constant
transformation
less
reactive
atropisomer
into
more
one,
then
single
enantiopure
product
presence
an
appropriate
organocatalyst.
This
review
summarizes
recent
advancements
on
topic,
including
their
scopes,
limitations,
mechanisms,
applications
provides
some
insights
further
developments.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(12), P. 2403 - 2408
Published: March 19, 2024
The
catalytic
atroposelective
synthesis
of
axially
chiral
heterobiaryls
was
first
developed
through
the
direct
one-step
dynamic
kinetic
condensation
reaction
with
simple
transformation
C═O
bond
to
C═N
bond,
delivering
a
series
novel
heterobiaryl
oxime
ethers.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(28)
Published: May 16, 2024
Abstract
Axially
chiral
biaryl
scaffolds
are
important
in
pharmaceuticals,
natural
products,
and
asymmetric
synthesis.
Atroposelective
ring‐opening
of
configurationally
labile
reagents
via
dynamic
kinetic
transformation
provides
a
valuable
approach
to
access
axially
atropisomers.
This
review
summarizes
seminal
contributions
recent
advancements
on
this
topic
based
the
use
different
types
reagents.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
366(4), P. 909 - 915
Published: Dec. 23, 2023
Abstract
A
highly
enantioselective
biocatalytic
dynamic
kinetic
resolution
(DKR)
of
2‐(quinoline‐8‐yl)
3‐methylbenzaldehydes
and
1‐naphthaldehydes
is
described.
The
reaction
proceeds
by
atroposelective
carbonyl
reduction
catalyzed
commercial
ketoreductases
(KREDs),
generally
reaching
high
conversions
excellent
enantiomeric
excesses.
Both
atropoisomers
the
final
alcohols
can
be
obtained
a
proper
selection
biocatalyst.
DKR
strategy
relies
in
racemization
stereogenic
axis
that
takes
place
thanks
to
transient
Lewis
acid‐base
interaction
(LABI)
between
nitrogen
quinoline
group.
