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
Atroposelective [4+1] Annulation for the Synthesis of Isotopic Isoindolinones Bearing both Central and Axial Chirality
Chemical Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
Isotopically
chiral
molecules
have
drawn
much
attention
due
to
their
practical
applications
in
drug
discovery.
However,
existing
studies
this
area
are
mainly
limited
centrally
and
H/D
exchange.
Herein,
we
report
a
phosphoric
acid-catalyzed
atroposelective
[4+1]
annulation
of
ketoaldehydes
1H-indol-1-amines.
By
means
strategy,
series
D-
18O-labeled
atropisomers
featuring
both
central
axial
chiralities
synthesized
with
high
enantioselectivities
diastereoselectivities
good
excellent
isotopic
incorporation.
Experimental
density
functional
theory
suggest
that
the
reaction
involves
sequential
condensation,
cyclization
isomerization
cascade,
which
second
step
is
enantio-determining
process.
Язык: Английский
Trifluoromethyl Group (CF3) Induced Regioselective Larock Indole Synthesis from Unsymmetric β-CF3-1,3-enynes
Yan‐Hua Qiu,
Peng-Xiang Ma,
Wen‐Hao Shao
и другие.
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 24, 2025
The
indole
skeleton
exists
widely
in
natural
products,
pharmaceuticals,
and
materials.
We
disclose
here
a
trifluoromethyl
group
induced
regioselective
Larock
synthetic
method
from
unsymmetric
2-CF3-1,3-enynes.
presence
of
is
determinable
for
the
regioselectivity.
Once
CF3
was
replaced
with
methyl
or
phenyl
group,
ratio
1:1
to
1:1.4
isomers
were
obtained.
This
strategy
features
good
regioselectivity,
broad
substrate
scope,
high
functional
tolerance.
protocol
reported
offers
an
alternative
solution
rare
3,4-functionalization
products
further
transformed
show
distinctive
reactivity
hydroboration–oxidation
hydro-bromination.
Язык: Английский
Recent Advances in Palladium-Catalyzed Enantioselective Cyclization for the Construction of Atropisomers
Catalysts,
Год журнала:
2025,
Номер
15(4), С. 320 - 320
Опубликована: Март 27, 2025
Axially
chiral
structures
have
become
increasingly
common
in
modern
materials
and
pharmaceuticals,
especially
as
ligands
organocatalysts,
highlighting
their
growing
significance.
In
the
field
of
pharmaceutical
research,
there
are
several
notable
examples
worth
highlighting,
such
antibiotics
vancomycin,
Knipholone,
Mastigophorene
A.
Over
past
decade,
availability
axially
compounds
has
significantly
improved
through
advancements
existing
strategies
introduction
catalytic
atroposelective
synthesis
concepts.
These
synthetic
not
only
broaden
scope
chemical
reactions,
but
also
facilitate
construction
frameworks
with
high
application
value.
Currently,
various
methods
available
for
achieving
stereoselective
under
catalyst
control,
including
desymmetrization,
(dynamic)
kinetic
resolution,
cross-coupling
de
novo
ring-forming
synthesis.
This
paper
focuses
on
recent
advances
constructing
atropisomers
palladium-catalyzed
asymmetric
cyclization
strategies.
Язык: Английский
Palladium-Catalyzed Asymmetric Larock Isoquinoline Synthesis to Access Axially Chiral 3,4-Disubstituted Isoquinolines
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(40), С. 27809 - 27818
Опубликована: Сен. 26, 2024
Larock
isoquinoline
synthesis
is
one
of
the
most
efficient
and
straightforward
approaches
to
construction
3,4-disubstituted
isoquinolines.
However,
there
have
been
no
asymmetric
versions
for
axially
chiral
isoquinolines
since
their
initial
report
in
2001.
Herein,
we
documented
first
example
an
by
employing
Pd(OAc)
Язык: Английский
Rhodium-Catalyzed Regioselective [4 + 2] Cycloaddition of Ynamines and 2-(Cyanomethyl)phenylboronates
Organic Letters,
Год журнала:
2024,
Номер
26(31), С. 6586 - 6590
Опубликована: Июль 30, 2024
A
rhodium-catalyzed
[4
+
2]
cycloaddition
of
ynamines
and
2-(cyanomethyl)phenylboronates
has
been
developed,
leading
to
efficient
excellent
regioselective
synthesis
valuable
indole-linked
aromatic
compounds
in
a
concise
flexible
approach.
Interestingly,
this
strategy
was
successful
the
construction
C···N
axially
chiral
indoles
with
high
enantiocontrol
by
introduction
new
phosphoramidite
ligand
(Xie-Phos).
Язык: Английский
Site Specific C3‐Alkenylation of Indoles Mediated by in situ C‐H Iodination
Asian Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 29, 2024
Abstract
The
C3‐alkenylation
of
indoles
have
been
developed
by
means
a
novel
in
situ
iodination
tactic
which
is
capable
mediating
the
Heck
coupling
with
alkenes.
method
features
specific
site‐selectivity
oriented
C−I
bond,
high‐step
efficiency
without
pre‐functionalization
for
C‐halogen
bond
construction,
as
well
highly
general
tolerance
to
different
terminal
alkenes,
including
unactivated
acrylates,
acrylic
acid,
vinyl
sulfone
functionalized
natural
products.
Язык: Английский
Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 23, 2024
We
report
herein
an
efficient
and
site-selective
electrophilic
trifluoromethylthiolation
of
indolines.
In
the
absence
any
catalyst
or
additive,
C5-selective
could
proceed
at
room
temperature.
With
palladium
used
as
catalyst,
selectivity
was
reversed
completely,
giving
C7-selecive
trifluoromethylthiolated
products.
This
reaction
features
good
functional
group
tolerance,
simple
operation,
mild
conditions,
scale-up
application.
The
potential
utilities
products
were
shown
by
further
transformations.
Язык: Английский