Journal of Heterocyclic Chemistry,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Sept. 27, 2024
ABSTRACT
A
formal
[3
+
3]
cycloaddition
of
4‐hydroxycoumarins
with
propargylicalcohols
was
established
under
mild
conditions.
This
strategy
utilizes
diazonium
tetrafluoroborate
as
the
Lewis
acid
catalyst
and
provides
a
practical
approach
for
delivering
pyranocoumarin
derivatives
in
moderate
to
high
yield.
The
structure
cycloadduct
unequivocally
confirmed
by
single‐crystal
x‐ray
diffraction.
potential
synthetic
applications
this
were
also
highlighted
scale‐up
experiment
further
transformation.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(15)
Published: Feb. 7, 2023
This
study
establishes
the
first
organocatalytic
enantioselective
synthesis
of
axially
chiral
N,N'-bisindoles
via
phosphoric
acid-catalyzed
formal
(3+2)
cycloadditions
indole-based
enaminones
as
novel
platform
molecules
with
2,3-diketoesters,
where
de
novo
indole-ring
formation
is
involved.
Using
this
new
strategy,
various
were
synthesized
in
good
yields
and
excellent
enantioselectivities
(up
to
87
%
yield
96
ee).
More
importantly,
class
exhibited
some
degree
cytotoxicity
toward
cancer
cells
was
derived
into
phosphine
ligands
high
catalytic
activity.
provides
a
strategy
for
using
asymmetric
organocatalysis
realize
applications
such
scaffolds
medicinal
chemistry
catalysis.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(3)
Published: Nov. 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.
Precision Chemistry,
Journal Year:
2024,
Volume and Issue:
2(5), P. 208 - 220
Published: April 23, 2024
The
catalytic
asymmetric
diastereodivergent
synthesis
of
axially
chiral
2-alkenylindoles
was
established
via
phosphoric
acid-catalyzed
addition
reactions
C3-unsubstituted
with
Chemical Society Reviews,
Journal Year:
2024,
Volume and Issue:
53(22), P. 11165 - 11206
Published: Jan. 1, 2024
This
review
explores
the
fascinating
world
of
molecules
featuring
multiple
stereogenic
elements,
unraveling
different
strategies
designed
over
years
for
their
enantioselective
synthesis.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(10)
Published: Jan. 9, 2024
Abstract
We
present
the
first
example
of
electrocatalytic
three‐component
annulation–iodosulfonylation
indole‐tethered
1,6‐enynes
with
arylsulfonyl
hydrazides
and
KI
for
accessing
various
iodosulfonated
pyrrolo[1,2‐
a
]indoles
in
moderate
to
excellent
yields
high
stereospecificity.
This
electrosynthesis
opens
new
avenues
construction
skeleton
good
functional
group
compatibility
under
environmentally
benign
condition.
Based
on
control
experiments
cyclic
voltammetry
data,
we
suggested
plausible
reaction
mechanism
which
included
anodic
oxidation,
homolysis
iodide,
radical
addition,
5
‐
exo
dig
cyclization,
coupling
or
nucleophilic
attack
iodide
ions
cascade.
Chemical Synthesis,
Journal Year:
2023,
Volume and Issue:
3(1), P. 6 - 6
Published: Jan. 1, 2023
In
recent
years,
it
has
become
an
urgent
task
to
design
new
types
of
indole-based
platform
molecules
for
Nazarov-type
cyclizations
and
develop
organocatalytic
synthesizing
indole
derivatives.
To
fulfill
this
task,
in
work,
by
changing
the
alkynyl
terminal
substituent
from
t-Bu
aryl
group,
reactivity
3-alkynyl-2-indolylmethanols
is
modulated
serve
as
competent
substrates
Brønsted
acid-catalyzed
cyclization.
Based
on
reactivity,
first
cyclization
aryl-substituted
with
2-naphthols
accomplished,
leading
efficient
construction
a
class
axially
chiral
3,
4-dihydrocyclopenta[b]indole
scaffolds.
This
preliminary
investigation
asymmetric
provides
optional
strategy
atroposelective
cyclopenta[b]indole
addition,
preparation
optical
purity
established
through
resolution,
which
could
complementary
method
catalytic
approaches.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(11), P. 3893 - 3900
Published: Jan. 1, 2024
An
organocatalyzed
asymmetric
synthesis
of
C
sp2
–N
atropisomers
by
formal
–O
amination
has
been
established
from
3-alkynyl-3-hydroxyisoindolinones
and
1-methylnaphthalen-2-ols.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(10), P. 2857 - 2863
Published: Jan. 1, 2024
A
Rh-catalyzed
neighboring
group-directed
asymmetric
[2
+
2
2]
cycloaddition
of
1,6-diynes
and
ynamides
to
generate
C–N
axially
chiral
indole
derivatives
has
been
developed.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(29)
Published: May 3, 2024
The
chemistry
of
quinone
methides
formed
in
situ
has
been
flourishing
recent
years.
In
sharp
contrast,
the
development
and
utilization
biphenyl
are
rare.
this
study,
we
achieved
a
remote
stereocontrolled
1,12-conjugate
addition
for
first
time.
presence
suitable
chiral
phosphoric
acid,
alkynyl
were
generated
from
α-[4-(4-hydroxyphenyl)phenyl]propargyl
alcohols,
followed
by
enantioselective
with
indole-2-carboxylates.
strategy
enabled
alcohols
to
serve
as
efficient
allenylation
reagents,
providing
practical
access
broad
range
axially
allenes
bearing
(1,1'-biphenyl)-4-ol
unit,
which
previously
less
accessible.
Combined
control
experiments,
density
functional
theory
calculations
shed
light
on
reaction
mechanism,
indicating
that
enantioselectivity
originates
nucleophilic
methides.
Notably,
not
only
versatile
intermediates
was
confirmed
but
also
organocatalytic
1,12-addition
established.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(17), P. 3578 - 3584
Published: June 18, 2024
Abstract
A
copper‐catalyzed
radical‐induced
annulation‐halocyanomethylation
of
indole‐linked
1,6‐enynes
has
been
established
using
haloacetonitrile
as
radical
precursors,
enabling
the
synthesis
21
cyanomethylated
pyrrolo[1,2‐
a
]indoles
with
yields
ranging
from
42%
to
81%
and
Z
/
E
ratio
up
19:1.
Moreover,
by
adjusting
reaction
temperature,
variation
annulation‐bromobicyanomethylation
process
was
achieved,
resulting
in
production
12
bicyanomethylated
]indole
isomers
41–68%.
The
stereoisomeric
mixture
products
could
be
purified
their
pure
configurations
through
recrystallization.
proposed
mechanism
formulated
series
control
experiments.
