Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N─N chiral indoles
Science Advances,
Год журнала:
2024,
Номер
10(19)
Опубликована: Май 10, 2024
Atropisomeric
indoles
defined
by
a
N─N
axis
are
an
important
class
of
heterocycles
in
synthetic
and
medicinal
chemistry
material
sciences.
However,
they
remain
heavily
underexplored
due
to
limited
methods
challenging
stereocontrol
over
the
short
bonds.
Here,
we
report
highly
atroposelective
access
axially
chiral
via
asymmetric
Larock
reaction.
This
protocol
leveraged
powerful
role
phosphoramidite
ligand
attenuate
common
dissociation
original
reaction,
forming
with
excellent
functional
group
tolerance
high
enantioselectivity
palladium-catalyzed
intermolecular
annulation
between
readily
available
o
-iodoaniline
alkynes.
The
multifunctionality
prepared
allowed
diverse
post-coupling
transformations,
affording
broad
array
functionalized
indoles.
Experimental
computational
studies
have
been
conducted
explore
reaction
mechanism,
elucidating
enantio-determining
rate-limiting
steps.
Язык: Английский
Catalytic atroposelective synthesis of indolyl quinazolinones bearing N–N/C–C diaxes
Science China Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 9, 2025
Язык: Английский
Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis
Chemical Science,
Год журнала:
2024,
Номер
15(33), С. 13240 - 13249
Опубликована: Янв. 1, 2024
The
enantioselective
and
diastereoselective
synthesis
of
atropisomeric
hydrazides
with
defined
vicinal
central
axial
chirality
via
ternary
catalysis
in
a
one-pot
process
is
reported.
Язык: Английский
Synthesis of N–N Axially Chiral Pyrrolyl-oxoisoindolin via Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution
Organic Letters,
Год журнала:
2024,
Номер
26(29), С. 6179 - 6184
Опубликована: Июль 18, 2024
The
development
of
methods
for
the
asymmetric
synthesis
N-N
axial
chirality
remains
elusive
and
challenging.
Here,
we
disclose
a
method
construction
axially
chiral
pyrrolyl-oxoisoindolins
along
with
central
via
isothiourea
(ITU)-catalyzed
acylative
dynamic
kinetic
resolution
(DKR).
Axial
was
introduced
into
DKR
hemiaminals
first
time.
This
protocol
features
mild
conditions
excellent
yields
enantioselectivities.
Язык: Английский
Controlling Stereoselectivity with Noncovalent Interactions in Chiral Phosphoric Acid Organocatalysis
Chemical Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 18, 2025
Chiral
phosphoric
acids
(CPAs)
have
emerged
as
highly
effective
Brønsted
acid
catalysts
in
an
expanding
range
of
asymmetric
transformations,
often
through
novel
multifunctional
substrate
activation
modes.
Versatile
and
broadly
appealing,
these
benefit
from
modular
tunable
structures,
compatibility
with
additives.
Given
the
unique
types
noncovalent
interactions
(NCIs)
that
can
be
established
between
CPAs
various
reactants─such
hydrogen
bonding,
aromatic
interactions,
van
der
Waals
forces─it
is
unsurprising
catalyst
systems
become
a
promising
approach
for
accessing
diverse
chiral
product
outcomes.
This
review
aims
to
provide
in-depth
exploration
mechanisms
by
which
impart
stereoselectivity,
positioning
NCIs
central
feature
connects
broad
spectrum
catalytic
reactions.
Spanning
literature
2004
2024,
it
covers
nucleophilic
additions,
radical
atroposelective
bond
formations,
highlighting
applicability
CPA
organocatalysis.
Special
emphasis
placed
on
structural
mechanistic
features
govern
CPA-substrate
well
tools
techniques
developed
enhance
our
understanding
their
behavior.
In
addition
emphasizing
details
stereocontrolling
elements
individual
reactions,
we
carefully
structured
this
natural
progression
specifics
broader,
class-level
perspective.
Overall,
findings
underscore
critical
role
catalysis
significant
contributions
advancing
synthesis.
Язык: Английский
Catalytic Atroposelective Synthesis of N–N Axially Chiral Indolylamides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12559 - 12575
Опубликована: Авг. 27, 2024
The
catalytic
atroposelective
synthesis
of
N–N
axially
chiral
indolylamides
was
established
via
dynamic
kinetic
resolution,
which
makes
use
Lewis
base-catalyzed
asymmetric
acylation
N-acylaminoindoles
as
a
new
type
platform
molecule
with
anhydrides.
By
this
strategy,
series
were
synthesized
in
overall
good
yields
(up
to
98%)
excellent
enantioselectivities
99%
ee).
Moreover,
some
these
display
extent
anticancer
activity,
demonstrates
their
potential
application
medicinal
chemistry.
Therefore,
work
has
not
only
provided
strategy
for
the
monoaryl
indoles
but
also
offered
member
configurational
stability
and
promising
application,
thereby
solving
challenges
indoles.
Язык: Английский
Atroposelective Formal [2 + 5] Macrocyclization Synthesis for a Novel All-Hydrocarbon Cyclo[7] Meta-Benzene Macrocycle
Molecules,
Год журнала:
2024,
Номер
29(14), С. 3363 - 3363
Опубликована: Июль 17, 2024
A
novel
axially
chiral
all-hydrocarbon
cyclo[7]
(1,3-(4,6-dimethyl)benzene
(