Chemical Synthesis,
Journal Year:
2023,
Volume and Issue:
3(4)
Published: July 19, 2023
The
construction
of
d
3
-methylated
all-carbon
quaternary
stereocenters
has
been
successfully
developed
via
carbene-catalyzed
desymmetrization
prochiral
oxindolyl
1,3-diketones.
Three
new
stereogenic
centers
were
efficiently
constructed
with
satisfactory
outcomes.
Diverse
spiro-polycyclic
molecules
a
stereocenter
generated
in
good
to
excellent
yields
diastereoselectivities
and
enantioselectivities.
This
reaction
features
broad
substrate
scope,
functional-group
tolerance,
easy
scale-up.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 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.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(18), P. 3325 - 3329
Published: April 27, 2023
Herein,
an
NHC
(N-heterocyclic
carbene)-catalyzed
radical
coupling
reaction
between
aldehydes
and
azobis(isobutyronitrile)
(AIBN)
has
been
developed.
This
method
provides
efficient
convenient
approach
for
the
synthesis
of
β-ketonitriles
containing
a
quaternary
carbon
center
(31
examples,
up
to
>99%
yield)
utilizing
commercially
available
substrates.
protocol
features
broad
substrate
scope,
good
functional
group
tolerance,
high
efficiency
under
metal-free
mild
conditions.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: July 9, 2024
Abstract
Traditionally,
N
-aryl
phthalimides
are
synthesized
by
the
condensation
of
phthalic
anhydride
and
aniline
derivatives,
usually
proceeding
under
harsh
conditions.
The
alternative
mild
organocatalytic
strategies
for
their
synthesis
underdeveloped.
Herein,
we
demonstrate
atroposelective
via
traditional
N-C
C=O
disconnection
in-situ
acid
activation
phthalamic
subsequent
N-heterocyclic
carbene
(NHC)-catalyzed
amidation
allowed
well-decorated
in
excellent
yields
enantioselectivities.
Mechanistic
studies
reveal
addition
NHC
to
situ
generated
isoimides,
thus
introducing
a
unique
mode
generating
acylazoliums.
Interestingly,
both
enantiomers
product
can
be
accessed
from
same
using
pre-catalyst.
Moreover,
this
strategy
has
been
extended
maleimides.
An
approach
utilizing
N-heterocyclic
carbene
for
nitrile
formation
and
desymmetrization
reaction
is
developed.
The
process
involves
kinetic
resolution,
with
the
axially
chiral
aryl
monoaldehydes
obtained
in
moderate
yields
excellent
optical
purities.
These
can
be
conveniently
transformed
into
functionalized
molecules,
showing
great
potential
as
catalysts
organic
chemistry.
Molecules,
Journal Year:
2022,
Volume and Issue:
27(24), P. 9020 - 9020
Published: Dec. 17, 2022
The
development
of
diversity-oriented
synthesis
based
on
fluorine-containing
building
blocks
has
been
one
the
hot
research
fields
in
fluorine
chemistry.
β-CF3-1,3-enynes,
as
type
blocks,
have
attracted
more
attention
last
few
years
due
to
their
distinct
reactivity.
Numerous
value-added
trifluoromethylated
or
non-fluorinated
compounds
which
biologically
relevant
structural
motifs,
such
O-,
N-,
and
S-heterocycles,
carboncycles,
fused
polycycles,
multifunctionalized
allenes
were
synthesized
from
these
blocks.
This
review
summarizes
most
significant
developments
area
organofluorine
providing
a
detailed
overview
current
state
art.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(4), P. 688 - 693
Published: Jan. 20, 2023
A
carbene-catalyzed
reaction
to
synthesize
a
chiral
quinazolinone
with
new
activation
mode
of
an
"aniline-like"
N-H
moiety
is
disclosed.
Addition
the
nitrogen
atom
diphenyl
o-aminobenzaldehydes
via
NHC
imines
leads
quinazolinones
high
yields
and
optical
purities.
The
acidity
was
extremely
increased
through
formation
acyl
azolium
intermediate,
which
investigated
by
DFT
calculations.
Moreover,
were
found
have
fluorescence
quantum
efficiency.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 6, 2024
A
general
and
practical
route
to
the
synthesis
of
β-keto
amino
acid
derivatives
from
aldehydes
bench
stable
imine
surrogates
is
presented.
Following
interrupted
Polonovski
strategy,
formed
in
situ
was
trapped
by
catalytically
generated
Breslow
intermediate
an
aza
benzoin
reaction.
The
present
strategy
has
been
extended
formal
florfenicol
en
vancomycin.
functionalization
synthesized
highlights
applicability
current
methodology.
