Copper‐Catalyzed Desymmetric Alkyne–Azide Cycloaddition to Access Axially Chiral Biaryls
European Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 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.
Language: Английский
Catalytic dynamic kinetic reductive addition of simple aldehydes and aldimines with heterobiaryl triflates: harnessing both central and axial chirality
Organic & Biomolecular Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
A
nickel-catalyzed
intramolecular
dynamic
kinetic
resolution
(DKR)
strategy
has
been
developed
for
the
enantioselective
synthesis
of
axially
chiral
heterobiaryls
from
racemic
azabiaryl
triflates.
Using
a
reductive
addition
mechanism,
this
method
controls
both
axial
and
central
chirality,
offering
broad
substrate
scope,
excellent
enantioselectivity,
atroposelectivity.
The
resulting
were
effectively
employed
as
organocatalysts
ligands
in
asymmetric
transformations,
highlighting
their
synthetic
utility.
Mechanistic
studies
indicate
synergy
between
nickel-mediated
stereochemical
inversion,
addressing
challenges
concurrent
control.
Language: Английский