Synlett,
Journal Year:
2023,
Volume and Issue:
35(09), P. 997 - 1000
Published: Nov. 13, 2023
Abstract
A
cooperative
catalytic
process
through
palladium
and
Brønsted
acid
activation
is
developed
for
the
conjugate
addition
of
cyclic
β-keto
esters
to
azoalkenes
directly
followed
by
hemiaminal
formation
upon
cyclization.
This
transformation
enabled
utilizing
chiral
Pd-aqua
complexes
as
combined
acid–base
catalysts.
Thus,
bicyclic
highly
functionalized
dihydropyrroles
with
two
contiguous
quaternary
stereogenic
centers
are
formed
in
excellent
yields
single
diastereomers
exceptional
enantioselectivity.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(12), P. 9244 - 9253
Published: June 3, 2024
Catalytic
asymmetric
dearomatization
(CADA)
is
a
powerful
tool
for
the
rapid
construction
of
complex
chiral
three-dimensional
cyclic
molecules
featuring
quaternary
carbon
centers
from
readily
available
arenes.
However,
ubiquitous
nonfunctionalized
1-naphthols
to
afford
remains
challenging
and
undeveloped.
This
study
reports
dearomative
[4
+
1]
spiroannulation
via
copper
catalysis.
reaction
features
highly
chemo-,
regio-,
stereoselective
nucleophilic
addition
intramolecular
annulation
cascade
reactive
π-extended
copper-allenylidene,
thus
enabling
practical
synthesis
range
valuable
spirocyclic
enones
bearing
stereocenter
with
high
efficiency.
Furthermore,
this
protocol
applicable
phenols.
Control
experiments
supported
substitution-annulation
mechanism
by
excluding
process
involving
1,3-sigmatropic
shift.
Preliminary
biological
activity
studies
indicated
that
synthesized
hold
significant
promise
as
anticancer
agents
inducing
tumor
cell
apoptosis.
Advanced Science,
Journal Year:
2023,
Volume and Issue:
10(35)
Published: Oct. 23, 2023
Abstract
Herein,
the
first
diversity‐oriented
catalytic
asymmetric
dearomatization
of
indoles
with
o
‐quinone
diimides
(
‐QDIs)
is
reported.
The
(CADA)
one
research
focuses
in
terms
structural
and
biological
importance
dearomatized
indole
derivatives.
Although
great
achievements
have
been
made
target‐oriented
CADA
reactions,
reactions
are
regarded
as
more
challenging
remain
elusive
due
to
lack
synthons
featuring
multiple
reaction
sites
difficulty
precise
control
chemo‐,
regio‐,
enantio‐selectivity.
In
this
work,
‐QDIs
employed
a
versatile
building
block,
enabling
chemo‐divergent
dearomative
arylation
[4
+
2]
cycloaddition
indoles.
Under
catalysis
chiral
phosphoric
acid
mild
conditions,
various
indolenines,
furoindolines/pyrroloindolines,
six‐membered‐ring
fused
indolines
collectively
prepared
good
yields
excellent
enantioselectivities.
This
synthesis
protocol
enriches
chemistry
offers
new
opportunities
for
reactions.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(20), P. 4238 - 4243
Published: March 16, 2024
Abstract
The
catalytic
asymmetric
dearomative
arylation
of
2‐naphthols
enabled
by
the
unconventional
reactivity
o
‐quinone
diimides,
i.
e.
1,4‐conjugate
addition
on
quinone
sp
2
hybridized
carbon,
has
been
established.
Under
catalysis
chiral
phosphoric
acid,
various
cyclohexaenones
bearing
an
all‐carbon
quaternary
stereocenter
have
prepared
with
excellent
yields
and
enantioselectivities.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 26, 2025
The
[2,3]-sigmatropic
rearrangement
has
been
widely
utilized
to
construct
C-S
bonds.
Herein,
we
report
an
enantioselective,
intermolecular,
and
noncarbenoid
of
sulfonium
ylides
using
azoalkenes.
This
process
features
a
broad
substrate
scope,
high
efficiency,
excellent
enantioselectivity,
achieving
yields
up
99%
enantiomeric
excess
(ee)
96%.
Furthermore,
the
protocol
demonstrated
good
scalability.
Magnetic Resonance in Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 6, 2025
ABSTRACT
Determining
the
constitution
and
configuration
is
a
critical
step
in
characterizing
structure
of
small
molecules.
In
addition
to
classical
nuclear
magnetic
resonance
(NMR)
method
conducted
isotropic
solutions,
emerging
anisotropic
NMR
parameters
such
as
residual
dipolar
couplings
(RDCs)
were
also
employed
clarify
structures
organic
These
RDCs
not
only
confirmed
that
unexpectedly
synthesized
product
was
quinazolinone
but
validated
relative
diastereoisomeric
hydroindole
polyarylisocyanide
lyotropic
liquid
crystalline
solution
through
induction
anisotropy.
Singular
value
decomposition
(SVD)
fit
experimental
RDC
data
against
low‐energy
conformational
sets
an
unexpected
synthetic
product,
which
calculated
using
density
functional
theory
(DFT).
This
analysis
aimed
identify
correct
molecular
connection
sites.
Furthermore,
applied
determine
between
two
possible
diastereoisomers.
ChemCatChem,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 24, 2025
Abstract
The
combination
of
a
gold(I)
catalyst
with
small
amount
ionic
liquid
as
solvent
creates
catalytic
system
able
to
efficiently
promote
the
direct
synthesis
coumarins
from
phenols
and
alkynoic
acids/esters,
through
reaction
sequence
involving
gold‐catalyzed
intermolecular
alkyne
hydroarylation
followed
by
intramolecular
thermal/acid
catalyzed
(trans)esterification.
is
highly
atom
economical
works
well
under
mild
conditions,
relatively
short
times
<
1%
Au,
particularly
in
case
substituted
electron‐donating
groups
propiolic
acid
substrates.
Furthermore,
gold/IL
proved
recoverable
recyclable.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(13), P. 3516 - 3524
Published: Jan. 1, 2024
Steric
hindrance-regulated
double
dearomatization
reaction
of
non-functionalized
phenols
and
propargylic
alcohols
for
the
efficient
synthesis
polycyclic
diketones
is
reported.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(29), P. 6290 - 6294
Published: July 18, 2024
Strategies
that
fully
convert
available
racemic
substrates
into
valuable
enantioenriched
products
are
urgently
needed
in
organic
synthesis.
Reported
herein
is
the
first
parallel
kinetic
asymmetric
transformation
of
cyclohexadienones.
Racemic
cyclohexadienones
diastereoselectively
converted
a
new
pair
transient
dienol
intermediates,
which
then
protonated
by
chiral
phosphoric
acid
to
deliver
two
sets
hydroindole
bearing
quaternary
stereocenter
with
generally
excellent
enantioselectivity.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1685 - 1691
Published: Jan. 1, 2024
Reported
herein
is
the
first
diaza-[1,2]-Wittig
rearrangement-enabled
dearomative
spiroannulation
reaction
of
indoles.
This
protocol
features
metal-free
conditions,
a
redox-neutral
process,
broad
substrate
scope,
and
good
yield.
