Copper‐Catalyzed Desymmetric Alkyne–Azide Cycloaddition to Access Axially Chiral Biaryls
European Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 7, 2025
Abstract
Axially
chiral
biaryls
are
an
important
class
of
structural
units
widely
used
in
natural
product
synthesis,
drug
design,
and
as
ligands
for
asymmetric
catalysis.
Although
significant
progress
has
been
made
the
synthesis
axially
biaryls,
some
them
still
limited
to
narrow
substrate
ranges,
low
efficiency,
moderate
stereocontrol.
Herein,
we
describe
a
highly
efficient
route
prepare
atropisomeric
with
triazole
alkyne
modules
through
desymmetrization
prochiral
dialkynyl
diaryls
utilizing
cyclobutyl‐bridge
box
conjunction
copper
salts.
The
process
mild
conditions,
good
functional‐group
tolerance,
can
obtain
wide
array
valuable
biaryl
derivatives
excellent
yields
enantioselectivities.
Язык: Английский
Enantioselective Desymmetrization of Biaryls via Cooperative Photoredox/Brønsted Acid Catalysis and Its Application to the Total Synthesis of Ancistrobrevolines
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 5, 2025
Photoredox
catalysis
has
emerged
as
a
powerful
tool
for
forming
and
breaking
chemical
bonds,
further
taking
hold
with
its
integration
asymmetric
catalysis.
While
the
dual-catalytic
approach
led
to
successful
examples
of
control
stereogenic
centers,
axes
remained
underexplored.
In
this
study,
an
acylimine
intermediate
was
generated
through
photoredox
catalysis,
symmetric
substrate,
2-arylresorcinol,
desymmetrized
aid
chiral
phosphoric
acid
Using
approach,
center
axis
were
successfully
controlled
provide
natural-product-driven
compound.
The
origins
enantioselectivity
diastereoselectivity
investigated
density
functional
theory
study
four
possible
enantiodetermining
transition
states.
Consequently,
first
total
syntheses
ring-contracted
naphthylisoquinoline
alkaloid
ancistrobrevolines
A
B
accomplished
concisely.
This
provides
not
only
novel
methodology
strategy
synthesize
alkaloids
but
also
direction
advance
catalytic
research
synthesis
studies.
Язык: Английский
Ni-Catalyzed Desymmetric Radical Cross-Coupling Reaction to Access Axially Chiral Biaryls
Yue-Die Zhu,
Zhen-Yao Dai,
Min Jiang
и другие.
ACS Catalysis,
Год журнала:
2024,
Номер
14(18), С. 13860 - 13866
Опубликована: Сен. 3, 2024
The
synthesis
of
axially
chiral
biaryls
continues
to
garner
significant
attention
in
the
scientific
community.
In
this
work,
we
introduce
a
Ni-catalyzed
desymmetrization
strategy
for
prochiral
dibromoarenes,
conducted
under
mild
reaction
conditions
and
with
good
functional
group
tolerance.
This
method
allows
from
readily
available
coupling
partners,
such
as
aldehydes,
ethers,
unactivated
alkyl
bromides.
Moreover,
has
been
successfully
applied
concise
enantioenriched
azulene-embedded
[7]helicene,
promising
organic
optoelectronics
material.
Язык: Английский
Construction of Axially Chiral 4-Aminoquinolines by Cycloaddition and Central-to-Axial Chirality Conversion
Organic Letters,
Год журнала:
2024,
Номер
26(46), С. 9984 - 9989
Опубликована: Ноя. 14, 2024
A
two-step
strategy
has
been
established
for
the
enantioselective
synthesis
of
4-aminoquinolines
possessing
axial
chirality.
This
approach
involves
a
chiral
phosphoric
acid-catalyzed
cycloaddition,
followed
by
DDQ
oxidation
step.
The
method
offers
efficient
access
to
variety
1,1'-biaryl-2,2'-amino
alcohol
derivatives
in
excellent
yields
and
enantioselectivities
(up
98%
yield
93%
ee).
Furthermore,
synthetic
transformation
products
was
also
investigated.
Язык: Английский