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.
Organic Letters,
Год журнала:
2024,
Номер
26(4), С. 917 - 921
Опубликована: Янв. 18, 2024
A
chiral
carbene-catalyzed
chemo-
and
enantioselective
reaction
with
racemic
biaryl
aldehydes
α-bromoenals
is
developed
for
access
to
axially
2-arylbenzaldehydes
through
atroposelective
dynamic
kinetic
resolution
(DKR)
processes.
This
DKR
strategy
can
tolerate
a
broad
scope
of
substrates
diverse
functionalities.
The
2-aryl
benzaldehyde
products
generally
afford
moderate
good
yields
enantioselectivities.
molecules
afforded
from
the
current
approach
are
variable
simple
transformations
functional
excellent
optical
purities.
ACS Catalysis,
Год журнала:
2024,
Номер
14(11), С. 8176 - 8183
Опубликована: Май 10, 2024
Axially
chiral
bridged
biaryls
represent
an
important
subset
of
axially
biaryl
scaffolds
in
fields
ranging
from
organic
synthesis
to
biochemistry
materials
science.
While
numerous
catalytic
strategies
have
been
elucidated
for
the
construction
axial
chirality,
enantioenriched
form
remains
underdeveloped.
Herein,
we
demonstrate
approach
synthesize
diverse
through
nickel-catalyzed
kinetic
asymmetric
cleavage
unactivated
aromatic
C–O
bond.
The
system
features
mild
reaction
conditions,
high
resolution
efficiency,
and
versatile
post-functionalizations.
Mechanistic
studies
reveal
impact
nickel
catalyst's
chirality
on
stereochemical
output
this
transformation.
Abstract
Axially
chiral
furan‐based
scaffolds
have
been
recognized
as
a
class
of
important
five‐membered
heteroaryl
atropisomers,
and
developing
catalytic
atroposelective
reactions
for
constructing
this
is
highly
desirable.
However,
the
construction
such
rather
underdeveloped
due
to
existence
great
challenges
remote
ortho
‐substituents
weak
configurational
stability.
To
overcome
these
challenges,
synthetic
chemists
recently
paid
attention
research
field,
number
axially
constructed
via
using
different
strategies.
This
concept
summarized
advances
in
field
pointed
out
remaining
which
will
promote
further
development
emerging
field.
Chemical Science,
Год журнала:
2024,
Номер
15(23), С. 8880 - 8887
Опубликована: Янв. 1, 2024
Axially
chiral
eight-membered
bridged
(hetero)biaryls
have
been
constructed
via
organocatalytic
intramolecular
[3
+
2]
cycloaddition
of
innovative
(hetero)biaryl
aldehydes
with
3-amino
oxindole
hydrochlorides.
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.
