Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(3)
Опубликована: Ноя. 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.
Язык: Английский
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
Construction of axial and point chirality through Ni-catalyzed sila-cycloaddition reaction via desymmetrization and (dynamic) kinetic resolution
Science China Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 6, 2025
Язык: Английский
Access to distal biaxial atropisomers by iridium catalyzed asymmetric C–H alkylation
Chemical Science,
Год журнала:
2024,
Номер
15(33), С. 13541 - 13549
Опубликована: Янв. 1, 2024
Herein,
we
report
an
iridium-catalyzed
asymmetric
C–H
activation
combined
with
a
desymmetrization
strategy
for
synthesizing
distal
biaxial
atropisomers
excellent
stereoselectivity,
displaying
promising
photophysical
and
chiroptical
properties.
Язык: Английский
Atroposelective synthesis of N–N axially chiral pyrrolyl(aza)-quinolinone by de novo ring formation
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
11(3), С. 726 - 734
Опубликована: Дек. 4, 2023
A
chiral
phosphoric
acid-catalyzed
Paal–Knorr
reaction
was
achieved
for
constructing
axially
pyrrolyl(aza)quinolinones
with
‘6–5’-membered
rings
as
a
new
family
member
of
N–N
atropisomers.
Язык: Английский
Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds
Chinese Journal of Organic Chemistry,
Год журнала:
2024,
Номер
44(2), С. 349 - 349
Опубликована: Янв. 1, 2024
Enantioenriched
C-N
axial
chiral
compounds
are
ubiquitous
in
many
important
field,
such
as
natural
products,
drugs
and
ligands.Therefore,
efficient
construction
of
axis
chirality
through
asymmetric
catalytic
synthesis
has
attracted
more
attention
research
interest.In
this
review,
the
recent
progress
been
discussed,
mainly
from
three
aspects:
desymmetrization
prochiral
molecules
or
kinetic
resolution
racemates,
atroposelective
functionalization
axis,
coupling
reaction.The
topic
focuses
on
evolution
system
key
factors
control.The
existing
problems
future
development
direction
field
also
discussed.This
paper
is
a
timely
systematic
review
will
stimulate
extensive
interest.
Язык: Английский
Rh(III)-Catalyzed Diastereo- and Enantioselective Regiodivergent (Hetero)Arylamidation of (Homo)Allylic Sulfides
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(14), С. 9768 - 9778
Опубликована: Март 28, 2024
A
rhodium-catalyzed
3-component
conjunctive
diastereo-
and
regioselective
arylamidation
of
(homo)allylic
sulfides,
organon
boronic
acids,
dioxazolones
is
reported.
These
reactions
deliver
the
1,2-insertion
2,1-insertion
products,
respectively,
for
allylic
sulfides
homoallylic
sulfides.
The
enantioselective
terminal
internal
achieved,
furnishing
various
1,3-N,S
compounds
featuring
one
or
two
contiguous
stereocenters
in
high
yields
with
enantioselectivities.
Mechanistic
studies
suggest
a
change
turnover-limiting
selectivity-determining
steps
induced
by
native
easily
removable
sulfide
group.
Язык: Английский
Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field
Angewandte Chemie,
Год журнала:
2023,
Номер
136(3)
Опубликована: Ноя. 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.
Язык: Английский
Rhodium-catalyzed atropodivergent hydroamination of alkynes by leveraging two potential enantiodetermining steps
Science Advances,
Год журнала:
2024,
Номер
10(48)
Опубликована: Ноя. 27, 2024
A
pair
of
enantiomers
is
known
to
have
different
biological
activities.
Two
catalysts
with
opposite
chirality
are
nearly
always
required
deliver
both
enantiomeric
products.
In
this
work,
chiral
rhodium(III)
cyclopentadienyl
complexes
repurposed
as
efficient
for
enantiodivergent
and
atroposelective
hydroamination
sterically
hindered
alkynes.
Products
been
obtained
using
the
same
or
closely
analogous
catalyst
in
good
efficiency
excellent
enantioselectivity,
enantiodivergence
was
mainly
enabled
by
an
achiral
carboxylic
acid
its
silver
salt.
Mechanistic
studies
revealed
origin
ascribable
switch
enantiodetermining
step
(alkyne
insertion
versus
protonolysis)
under
control,
which
constitutes
a
previously
unidentified
working
mode
leveraging
two
elementary
steps.
Язык: Английский