The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(7), P. 4861 - 4876
Published: March 25, 2024
Cis-hydrobenzofurans,
cis-hydroindoles,
and
cis-hydrindanes,
privileged
structural
motifs
found
in
numerous
biologically
active
natural
synthetic
compounds,
are
efficiently
prepared
by
a
Rh(I)-catalyzed
cascade
syn-arylation/1,4-addition
protocol.
This
approach
starts
with
the
regioselective
syn-arylation
of
alkyne
tethered
to
2,5-hexadienone
moieties,
using
chiral
Rh(I)
catalyst
generated
situ
from
bicyclo[2.2.1]hepatadiene
ligand
L4f.
By
forging
two
new
carbon–carbon
bonds
introducing
centers,
resulting
alkenylrhodium
species
undergoes
desymmetrization
via
an
intramolecular
1,4-addition
reaction,
delivering
annulated
products
high
yields
enantioselectivities.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(14), P. 9829 - 9838
Published: July 11, 2023
The
development
of
chiral
ligands
to
fine-tune
the
stereocontrol
has
been
recognized
as
a
crucial
pillar
asymmetric
catalysis.
In
contrast
well-developed
pyridine–pyridine-type
and
pyridine–oxazoline-type
ligands,
oxazole–pyridine-type
have
rarely
exploited.
this
study,
class
[2.2]paracyclophane-based
planar-chiral
oxazole–pyridine
N,N-ligands
designed
synthesized.
These
presented
superior
performance
in
enantioselective
palladium-catalyzed
acetoxylative
cyclization
alkyne-tethered
cyclohexadienones,
providing
cis-hydrobenzofurans
that
belong
bioactive
molecules
with
potent
NF-κB
inhibition
broad
substrate
scope.
results
demonstrated
promising
potential
an
efficient
type
N,N-ligand
scaffold.
Chemistry - An Asian Journal,
Journal Year:
2021,
Volume and Issue:
17(4)
Published: Nov. 24, 2021
A
remarkable
growth
in
hypervalent
iodine-mediated
oxidative
transformations
as
stoichiometric
reagents
well
catalysts
has
been
well-documented
due
to
their
excellent
properties,
such
mildness,
easy
handling,
high
selectivity,
environmentally
friendly
nature,
and
stability.
This
review
aims
at
highlighting
the
asymmetric
dearomatization
reactions
involving
iodine
compounds.
The
present
article
summarizes
intra-
intermolecular
using
chiral
reagents/catalysts
followed
by
desymmetrization.
Nature Communications,
Journal Year:
2023,
Volume and Issue:
14(1)
Published: Aug. 25, 2023
Abstract
The
catalytic
asymmetric
dearomatization
(CADA)
reaction
has
proved
to
be
a
powerful
protocol
for
rapid
assembly
of
valuable
three-dimensional
cyclic
compounds
from
readily
available
planar
aromatics.
In
contrast
the
well-studied
indoles
and
naphthols,
phenols
have
been
considered
challenging
substrates
intermolecular
CADA
reactions
due
combination
strong
aromaticity
potential
regioselectivity
issue
over
multiple
nucleophilic
sites
(O,
C2
as
well
C4).
Reported
herein
are
chiral
phosphoric
acid-catalyzed
divergent
common
with
azoalkenes,
which
deliver
tetrahydroindolone
cyclohexadienone
products
bearing
an
all-carbon
quaternary
stereogenic
center
in
good
yields
excellent
ee
values.
Notably,
simply
adjusting
temperature
leads
chemo-divergent
(3
+
2)
alkylation
reactions.
Moreover,
stereo-divergent
synthesis
four
possible
stereoisomers
kind
achieved
via
changing
sequence
catalyst
enantiomers.
The Chemical Record,
Journal Year:
2021,
Volume and Issue:
21(12), P. 3689 - 3726
Published: June 19, 2021
The
development
of
transition-metal
catalyzed
enantioselective
and
diastereoselective
transformations
has
contributed
many
advances
in
the
field
synthetic
organic
chemistry.
Particularly,
stereoselective
desymmetrization
prochiral
cyclohexadienones
represents
a
powerful
strategy
for
accessing
highly
functionalized
stereochemically
enriched
scaffolds,
which
are
often
found
biologically
active
compounds
natural
products.
In
recent
years,
several
research
groups
including
our
group
have
made
significant
progress
on
desymmetrizations
2,5-cyclohexadienones.
this
account,
we
will
provide
an
overview
developments
area
employing
Pd,
Cu,
Rh,
Au,
Ag,
Ni,
Co,
Mn-catalysts.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(4), P. 839 - 844
Published: Jan. 22, 2024
An
efficient
method
for
the
stereoselective
synthesis
of
"all
center
substituted"
polycyclic
pyrazoles
from
alkynyl
cyclohexa-2,5-dienones
and
nonstabilized
diazoalkanes
via
sequential
[3
+
2]-cycloaddition/[1,5]-sigmatropic
rearrangement
aza-Michael
reactions
is
reported.
The
developed
process
highly
regioselective
stereoselective.
It
employs
a
wide
substrate
scope
to
furnish
structurally
diverse
linear
bridged
[4.4.n.0]
ring-fused
in
moderate
good
yields.
One-pot
gram-scale
syntheses
synthetic
transformations
have
also
been
showcased.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(9), P. 1812 - 1816
Published: Feb. 24, 2022
A
catalytic
asymmetric
desymmetrization
of
cyclohexadienones
was
accomplished
via
Van
Leusen
pyrrole
synthesis
in
the
presence
a
chiral
silver
catalyst.
The
ready
access
to
chiral-fused
derivatives
is
attributed
identification
suitable
isocyanomethyl
sulfone
surrogate,
NasMIC.
current
Ag(I)–chiral
phosphino-carboamide
ligand
system
can
be
extended
kinetic
resolution
racemic
cyclohexadienones,
capitalizing
on
differentiated
reactivity
quaternary
complexes
from
AgSbF6,
(L*),
cyclohexadienone,
and
