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.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 23, 2025
We
report
a
highly
regioselective
1,2-addition
of
P(O)-H
compounds
to
the
in
situ
generated
β,γ-alkynyl-α-ketimine
derived
from
3-alkynyl-3-hydroxyisoindolinones,
which
provided
general
protocol
for
preparation
3,3-disubstituted
isoindolinones
featuring
both
phosphoryl
and
alkynyl
groups
at
quaternary
carbon
center.
The
use
only
2-5
mol
%
an
inexpensive
catalyst
(In(ClO4)3·8H2O
or
Bi(OTf)3)
allowed
smooth
output
desired
products
under
mild
conditions
(25
°C,
0.5-24
h)
with
broad
substrate
scope
(35
examples)
up
>99%
yield.
obtained
could
be
further
elaborated
based
on
alkyne
moiety.
initial
asymmetric
trial
indicated
that
BINOL-derived
CPA
enable
enantioselective
induction
46%
yield
77%
ee.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 26, 2025
Organocatalytic
enantioselective
formal
nucleophilic
substitution
reactions
of
α-(2-hydroxynaphthalen-8-yl)propargyl
alcohols
with
1-(1H-indol-3-yl)naphthalen-2-ols
have
been
established
for
the
first
time.
With
aid
a
suitable
chiral
phosphoric
acid,
alkynyl
8-methylenenaphthalen-2(8H)-one
was
formed
in
situ
from
corresponding
alcohol,
followed
by
1,6-conjugate
additions
to
afford
number
enantioenriched
(Ra,Sc)-2,3-disubstituted
indoles
50-80%
yields
81-93%
ee
and
(Sa,Sc)-2,3-disubstituted
18-40%
79-96%
ee.
Notably,
these
products
were
characterized
presence
functional
groups,
including
indole,
naphthol,
units,
while
exhibiting
both
axial
central
chirality.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(8), P. 1670 - 1706
Published: Feb. 29, 2024
Abstract
The
Friedel‐Crafts
reaction
stands
as
a
powerful
synthetic
tool
for
C−H
functionalization
of
aromatic
feedstocks,
which
is
conventionally
realized
through
electrophilic
alkylation
and
acylation.
burgeoning
interests
in
axially
chiral
compounds
across
diverse
fields
have
spurred
extensive
exploration
this
classic
transformation
catalytic
atroposelective
synthesis.
Consequently,
the
past
decade
has
witnessed
rapid
expansion
various
non‐canonical
reactions,
including
arylation,
alkenylation,
halogenation,
sulfenylation,
amination
aryl
bonds,
thereby
delving
into
new
chemical
spaces.
A
range
methods
been
devised
these
significant
arene
functionalization.
This
review
provides
comprehensive
overview
cutting‐edge
synthesis
atropoisomers
categorized
three
parts
based
on
type
bond
formation
aromatics:
C(
sp
2
)−C(
3
)
formations,
formations
)−heteroatom
formations.
richness
electrophiles
modulation
atroposelectivity
by
organocatalysts,
particularly
Brønsted
acids,
are
elucidated.
We
anticipate
that
repertoire
asymmetric
will
continue
to
flourish
be
demonstrated
not
only
scientific
researches
but
also
industrial
organic
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(42), P. 7745 - 7750
Published: Oct. 16, 2023
A
rhodium-catalyzed
carbene
N-H
insertion
protocol
for
simultaneously
controlling
the
C-N
axial
and
spiro-central
chiralities
is
disclosed,
resulting
in
rapid
assembly
of
enantiopure
N-arylindolinone-spiroacetal
derivatives
high
yields
with
excellent
enantioselectivities.
This
promising
strategy
features
chiral
axis,
chirality,
functional
group
tolerance,
late-stage
diversification.
DFT
calculations
indicate
that
axial-chirality-determining
step
1,5-H
shift
regiospecifically
caused
by
spirocycle.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(17), P. 3453 - 3458
Published: Jan. 1, 2024
A
HOTf
or
Fe(OTf)
3
-catalyzed
dehydrative
alkynylation
of
3-hydroxyisoindolinones
with
terminal
alkynes
was
developed,
which
represents
a
brand-new
procedure
for
the
synthesis
3-alkynylated
3,3-disubstituted
isoindolinones.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(29)
Published: May 3, 2024
Abstract
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.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12559 - 12575
Published: Aug. 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,
Journal Year:
2024,
Volume and Issue:
26(36), P. 7667 - 7671
Published: Aug. 29, 2024
A
chiral
Brønsted
acid
catalyzed
asymmetric
aza-Piancatelli
rearrangement
of
3-furyl-3-hydroxyisoindolinones
with
anilines
has
been
developed,
enabling
the
divergent
construction
spiro-cyclopentenone-isoindolinones
in
high
yields
excellent
diastereo-
and
enantioselectivities
even
under
a
low
catalyst
loading
0.5
mol%.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
136(3)
Published: Nov. 2, 2023
Abstract
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.
Asian Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
13(6)
Published: March 12, 2024
Abstract
Two
different
skeletons
have
been
constructed
by
cyclization
of
α‐(3‐isoindolinonyl)
propargylic
alcohols
with
5‐aminoisoxazoles
bearing
N
‐substituents
under
the
relay
catalysis
Brønsted
acid
and
Lewis
acid.
This
method
provided
spiro‐isoindolinone‐dihydropyridines
moderate
to
high
yields
(up
99
%)
as
well
isoxazolo[4,5‐b]pyridines
in
good
86
%).
The
structures
two
products
were
determined
X‐ray
crystal
structural
analyses.
Moreover,
fluorescence
testing
proved
that
one
exhibited
aggregation
induced
emission
(AIE)
effect.
Finally,
control
experiments
revealed
possible
reaction
mechanism.
