Asian Journal of Organic Chemistry,
Год журнала:
2023,
Номер
12(5)
Опубликована: Апрель 12, 2023
Abstract
A
Pd‐catalyzed
coupling
reaction
from
o
‐alkynylanilines
and
‐(2,2‐dibromovinyl)anilines
for
the
synthesis
of
2,3′‐bisindoles
is
developed.
In
which,
‐ethynylaniline
was
used
as
3‐functionalized
indole
precursor
‐(2,2‐dibromovinyl)aniline
2‐functionalized
precursor.
This
protocol
exhibits
high
efficiency,
good
functional
group
tolerance
scalability
easily
accessible
starting
materials.
Precision Chemistry,
Год журнала:
2024,
Номер
2(5), С. 208 - 220
Опубликована: Апрель 23, 2024
The
catalytic
asymmetric
diastereodivergent
synthesis
of
axially
chiral
2-alkenylindoles
was
established
via
phosphoric
acid-catalyzed
addition
reactions
C3-unsubstituted
with
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(27)
Опубликована: Март 6, 2023
Atropisomeric
heterobiaryls
play
a
vital
role
in
natural
products,
chiral
ligands,
organocatalysts,
and
other
research
fields,
which
have
aroused
great
interest
from
chemists
recent
years.
Until
now,
growing
number
of
optically
active
based
on
indole,
quinoline,
isoquinoline,
pyridine,
pyrrole,
azole,
benzofuran
skeletons
been
successfully
synthesized
through
metal
or
organic
catalytic
cross-coupling,
functionalization
prochiral
racemic
heterobiaryls,
ring
formation.
Among
different
strategies
for
the
atroposelective
synthesis
strategy
formation
has
become
tool
toward
this
goal.
In
review,
we
summarize
enantioselective
axially
approaches,
such
as
cycloaddition,
cyclization,
chirality
conversion.
Meanwhile,
reaction
mechanism
corresponding
applications
are
also
discussed.
European Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 2, 2025
Abstract
This
review
collects
the
recent
developments
in
synthesis
of
chiral
heterocycles
through
enantioselective
silver‐catalyzed
transformations
published
since
2018.
It
demonstrates
power
silver
catalysts
as
special
mild
Lewis
acids
to
provide
an
impressive
diversity
reaction
pathways,
such
1,3‐dipolar
cycloadditions,
various
types
cyclizations,
along
with
a
wide
variety
more
complex
domino/tandem
reactions,
allowing
many
novel
heterocyclic
products
be
achieved
high
enantioselectivities.
Chemical Science,
Год журнала:
2023,
Номер
14(43), С. 12091 - 12097
Опубликована: Янв. 1, 2023
The
first
organocatalytic
atroposelective
synthesis
of
axially
chiral
N,N'-pyrrolylindoles
based
on
o-alkynylanilines
was
successfully
established
via
de
novo
indole
formation
catalyzed
by
phosphoric
acid
(CPA).
This
new
synthetic
strategy
introduced
CPA-catalyzed
asymmetric
5-endo-dig
cyclization
well-designed
containing
a
pyrrolyl
unit,
resulting
in
wide
range
high
yields
with
exclusive
regioselectivity
and
excellent
enantioselectivity
(up
to
99%
yield,
>20
:
1
rr,
95
5
er).
Considering
the
potential
biological
significance
N-N
atropisomers,
preliminary
activity
studies
were
performed
revealed
that
these
structurally
important
had
low
IC50
value
promising
impressive
cytotoxicity
against
several
kinds
cancer
cell
lines.
DFT
reveal
N-nucleophilic
mediated
CPA
is
rate-
stereo-determining
step,
which
ligand-substrate
dispersion
interactions
facilitate
axial
chirality
target
products.
ACS Catalysis,
Год журнала:
2024,
Номер
14(6), С. 4053 - 4065
Опубликована: Март 1, 2024
Chiral
recognition
for
the
synthesis
of
axially
chiral
biaryl
units
is
a
fundamental
and
challenging
topic
in
organic
synthesis.
Herein,
we
documented
that
an
efficient
O-ligand
exchange
between
catalyst
substrate
enabled
axial
asymmetric
aminopalladation/olefination
2-alkynylanilides
vinyl
trifluoromethanesulfonates,
providing
3-alkenylindoles
with
up
to
97%
ee
98%
yield.
This
protocol
features
mild
conditions,
broad
functional
group
tolerance,
scalability,
late-stage
modification
bioactive
molecules.
Experimental
computational
studies
hinted
(R)-BIDIME/Pd
complex
alkoxy
was
crucial
success
stereoselectivity
control.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(21), С. 4332 - 4357
Опубликована: Янв. 1, 2023
Silver
catalysis
offers
environmentally
friendly
and
simple
protocols
to
construct
N-heterocycles.
Inspired
by
its
appeal,
herein
we
have
summarized
developments
in
the
silver-catalyzed
synthesis
of
N-heterocycles
since
2019.
JACS Au,
Год журнала:
2023,
Номер
3(6), С. 1742 - 1754
Опубликована: Май 26, 2023
A
new
generation
of
chiral
gold(I)
catalysts
based
on
variations
complexes
with
JohnPhos-type
ligands
a
remote
C2-symmetric
2,5-diarylpyrrolidine
have
been
synthesized
different
substitutions
at
the
top
and
bottom
aryl
rings:
from
replacing
phosphine
by
N-heterocyclic
carbene
(NHC)
to
increasing
steric
hindrance
bis-
or
tris-biphenylphosphine
scaffolds,
directly
attaching
C2-chiral
pyrrolidine
in
ortho-position
dialkylphenyl
phosphine.
The
tested
intramolecular
[4+2]
cycloaddition
arylalkynes
alkenes
atroposelective
synthesis
2-arylindoles.
Interestingly,
simpler
led
formation
opposite
enantiomers.
binding
pockets
analyzed
DFT
calculations.
As
revealed
non-covalent
interaction
plots,
attractive
interactions
between
substrates
direct
specific
enantioselective
folding.
Furthermore,
we
introduced
open-source
tool
NEST,
specifically
designed
account
for
effects
cylindrical-shaped
complexes,
which
allows
predicting
experimental
enantioselectivities
our
systems.
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
42(7), С. 731 - 735
Опубликована: Ноя. 29, 2023
Comprehensive
Summary
Indole‐based
atropisomers
are
a
very
important
class
of
axially
chiral
compounds.
However,
the
atroposelective
synthesis
2‐arylindole
remains
largely
unexplored.
In
this
study,
we
report
successful
atropisomeric
2‐arylindoles
using
direct
amination
indoles
with
p
‐quinonediimines
in
presence
phosphoric
acid
as
catalyst.
Quinonediimine
acts
an
aminating
reagent
through
formal
polarity
inversion
imine.
The
malonate
group
on
2‐aryl
2‐indoles
was
found
to
be
essential
for
high
enantioselectivity
products.
This
could
due
additional
interaction
between
ester
and
catalyst,
well
intramolecular
hydrogen
bonding.
Our
findings
provide
new
strategy
asymmetric
construction
atropisomers.
Abstract
Atropisomeric
compounds
have
been
discovered
in
pharmaceuticals
and
materials
science,
their
enantioselective
syntheses
gained
tremendous
attention.
Among
strategies
for
catalytic
atroposelective
synthesis,
desymmetrization
provides
robust
straightforward
approaches
to
axially
chiral
biaryls.
Due
the
relative
ease
of
substrate
design
compared
other
strategies,
has
emerged
as
a
pivotal
stage
converting
fascinating
chemistry
into
its
counterpart,
despite
challenges
such
formation
achiral
products
by
subsequent
reactions
long
distance
between
reaction
site
stereogenic
axis.
This
review
offers
comprehensive
overview
recent
advancements
using
organo‐
metal
catalysts,
addressing
solutions,
aims
provide
insights
future
developments
this
field.
