Organic Letters,
Год журнала:
2023,
Номер
25(41), С. 7523 - 7528
Опубликована: Окт. 6, 2023
We
disclose
herein
a
highly
diastereo-
and
enantioselective
divergent
synthesis
of
seven-membered
biaryl-bridged
carbo-
oxacyclic
frameworks
by
utilizing
the
catalytic
ability
bifunctional
hydrogen-bonding
squaramide
organocatalysts.
Starting
with
same
biaryl
substrate
bearing
two
distinct
acceptor
sites
choosing
soft
or
hard
nucleophiles,
we
readily
accessed
dibenzocycloheptanes
5,7-dihydrodibenzo[c,e]oxepines
multiple
elements
chirality
via
domino
1,4/1,2-addition
1,2/oxa-Michael
addition
sequence,
respectively.
ACS Catalysis,
Год журнала:
2023,
Номер
13(4), С. 2565 - 2575
Опубликована: Фев. 6, 2023
We
present
herein
an
unprecedented
stereoselective
synthesis
of
triaryl-2-pyrones
with
monoaxial
or
contiguous
diaxes
from
readily
available
starting
materials.
This
N-heterocyclic
carbene
catalysis
method
adopts
atroposelective
annulation
2-aryketones
ynals
under
oxidative
conditions.
The
includes
the
construction
one
two
axes
in
a
single
operation,
achieves
step
economy,
and
affords
axially
chiral
moderate
to
good
yields,
high
excellent
enantioselectivities.
DFT
calculations
relative
energies
stereoisomers
rotational
barriers
were
performed.
Chemical Science,
Год журнала:
2024,
Номер
15(12), С. 4564 - 4570
Опубликована: Янв. 1, 2024
We
present
NHC-catalyzed
atroposelective
esterification
of
prochiral
dialdehydes,
delivering
enantioenriched
axially
chiral
diaryl
ethers.
Matched
kinetic
resolutions
amplify
the
enantioselectivity
by
removing
minor
enantiomers
via
over-functionalization.
ACS Catalysis,
Год журнала:
2024,
Номер
14(9), С. 6926 - 6935
Опубликована: Апрель 18, 2024
The
synthesis
of
N–N
axial
compounds
containing
aromatic
acyl
amides
using
common
acylation
reagents
remains
challenging.
We
describe
a
highly
atropenantioselective
N-aminoindoles
axes.
A
chiral
cyclic
isothiourea
is
used
as
the
sole
organic
catalyst
in
transformation
N-acylation
reaction.
Aroyl
chlorides
have
been
to
construct
atropisomeric
through
N-acylation.
N-aminoindole
products,
which
bear
stereogenic
axes,
were
synthesized
with
high
yields
and
enantioselectivities.
Some
enantiopure
products
exhibited
promising
antibacterial
activities
against
plant
pathogens.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(13), С. 1487 - 1492
Опубликована: Март 10, 2024
Comprehensive
Summary
We
report
herein
an
unprecedented
N
‐heterocyclic
carbene‐catalyzed
formal
[3
+
3]
annulation
of
ynals
with
‐Ts
indolin‐3‐ones
under
the
oxidation
condition
affording
functionalized
pyrano[3,2‐
b
]indol‐2‐ones.
The
alkynyl
acylazoliums
via
combination
a
carbene
in
presence
oxidate
proved
to
be
important
intermediates
for
success
this
transformation.
This
method
features
broad
substrate
scope
and
mild
conditions,
including
axially
chiral
skeletons
suitable
substitutions.
Nature Communications,
Год журнала:
2024,
Номер
15(1)
Опубликована: Май 30, 2024
Abstract
Bridged
chiral
biaryls
are
axially
compounds
with
a
medium-sized
ring
connecting
the
two
arenes.
Compared
plentiful
methods
for
enantioselective
synthesis
of
biaryl
compounds,
synthetic
approaches
this
subclass
bridged
atropisomers
limited.
Here
we
show
an
atroposelective
1,3-diaxial
eight-membered
terphenyl
through
Co/SPDO
(spirocyclic
pyrrolidine
oxazoline)-catalyzed
aerobic
oxidative
coupling/desymmetrization
reaction
prochiral
phenols.
This
catalytic
desymmetric
process
is
enabled
by
combination
earth-abundant
Co(OAc)
2
and
unique
SPDO
ligand
in
presence
DABCO
(1,4-diaza[2.2.2]bicyclooctane).
An
array
diaxial
terphenyls
embedded
azocane
can
be
accessed
high
yields
(up
to
99%)
excellent
enantio-
(>99%
ee)
diastereoselectivities
(>20:1
dr).
Chemical Society Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 18, 2024
This
tutorial
review
provides
an
overview
of
various
important
structural
features
and
reactivity
modes
NHCs
delves
deep
into
the
recent
advances
in
NHC-organocatalysis.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 24, 2025
An
N-heterocyclic
carbene-catalyzed
atroposelective
[3
+
3]
annulation
of
alkynyl
acylazoliums
with
benzothiazole
derivatives
has
been
developed
for
the
divergent
synthesis
axially
chiral
triaryl
2-pyranones
and
fused
2-pyridones.
The
regioselectivity
this
protocol
depends
on
structure
benzothiazoles
three
different
nucleophilic
centers.
obtained
frameworks
represent
a
new
class
arylheterocycle
atropisomers,
which
may
be
potentially
useful
in
medicinal
chemistry.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(39)
Опубликована: Июнь 20, 2023
The
development
of
catalytic
asymmetric
reaction
with
water
as
the
reactant
is
challenging
due
to
reactivity-
and
stereoselectivity-control
issues
resulted
from
low
nucleophilicity
small
size
water.
We
disclose
herein
a
chiral
phosphoric
acid
(CPA)
catalyzed
atroposelective
ring-opening
biaryl
oxazepines
A
series
undergo
CPA
hydrolysis
in
highly
enantioselective
manner.
key
for
success
this
use
new
SPINOL-derived
catalyst
high
reactivity
oxazepine
substrates
towards
under
acidic
conditions.
Density
functional
theory
calculations
suggest
that
proceeds
via
dynamic
kinetic
resolution
pathway
addition
imine
group
both
enantio-
rate-determining.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(28)
Опубликована: Май 16, 2024
Abstract
Axially
chiral
biaryl
scaffolds
are
important
in
pharmaceuticals,
natural
products,
and
asymmetric
synthesis.
Atroposelective
ring‐opening
of
configurationally
labile
reagents
via
dynamic
kinetic
transformation
provides
a
valuable
approach
to
access
axially
atropisomers.
This
review
summarizes
seminal
contributions
recent
advancements
on
this
topic
based
the
use
different
types
reagents.
