ACS Catalysis,
Год журнала:
2024,
Номер
unknown, С. 18378 - 18384
Опубликована: Ноя. 30, 2024
The
catalytic
asymmetric
transformation
of
nitrogen
atoms
to
prepare
heterocyclic
molecules
is
significant
value
in
organic
synthesis
and
biological
applications.
Here,
we
disclose
the
activation
atom
hydrazine-derived
hydrazone
via
an
N-heterocyclic
carbene
(NHC)
catalyst
for
highly
enantioselective
formal
cycloaddition
reactions.
range
NHC
catalysis
extends
across
several
(carbon
hetero)
diverse
chemical
bonds
(C═N
N–N
bonds)
activate
at
remote
sites
with
excellent
reactivity
(stereo)selectivity
control.
Our
strategy
activation,
along
NHC-bound
diaza-diene
intermediate
generated
during
process,
offers
alternative
solutions
synthesis.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(19), С. 5573 - 5604
Опубликована: Янв. 1, 2024
This
review
has
summarized
the
development
of
organocatalytic
asymmetric
[3
+
3]
cycloadditions
and
given
insights
into
remaining
challenges
to
promote
future
this
field.
Chemical Society Reviews,
Год журнала:
2024,
Номер
53(22), С. 11165 - 11206
Опубликована: Янв. 1, 2024
This
review
explores
the
fascinating
world
of
molecules
featuring
multiple
stereogenic
elements,
unraveling
different
strategies
designed
over
years
for
their
enantioselective
synthesis.
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.
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.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 24, 2025
An
N-heterocyclic
carbene-catalyzed
atroposelective
[3
+
3]
annulation
of
alkynyl
acylazoliums
with
benzothiazole
derivatives
has
been
developed
for
the
divergent
synthesis
axially
chiral
triaryl
2-pyranones
and
fused
2-pyridones.
The
regioselectivity
this
protocol
depends
on
structure
benzothiazoles
three
different
nucleophilic
centers.
obtained
frameworks
represent
a
new
class
arylheterocycle
atropisomers,
which
may
be
potentially
useful
in
medicinal
chemistry.
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Фев. 15, 2025
Methods
for
catalytically
constructing
of
N–N
axially
chiral
scaffolds
have
garnered
significant
attention
since
such
compounds
are
widely
present
in
natural
products,
bioactive
molecules,
and
organic
materials.
Herein,
we
report
a
highly
diastereoselective
enantioselective
organocatalyzed
[4
+
1]
annulation
method
synthesizing
diverse
valuable
isoindolinones
that
possessing
axial
central
chiralities.
This
methodology
uses
phosphoric
acid
as
bifunctional
catalyst
to
promote
cascade
sequence
involving
two
nucleophilic
additions,
dehydration,
dearomatization
processes.
Control
experiments
DFT
calculations
revealed
possible
mechanism
which
the
stereoselectivity-determining
step
is
likely
involve
irreversible
formation
hydroxy
biaryl
intermediate.
Additionally,
preliminary
biological
activity
studies
showed
some
these
potential
suppressing
tumor-cell
proliferation.
attention.
Here,
authors
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(19), С. 5437 - 5442
Опубликована: Янв. 1, 2024
Herein,
we
present
an
enantioselective
synthesis
of
N
-aminoindoles
bearing
a
N–N
axis
via
chiral
isothiourea
catalyzed
asymmetric
-acylation.
Notably,
some
the
products
exhibited
promising
cytotoxicity
activities
against
cancer
cell
lines.
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.
