The
present
study
reports
an
asymmetric
NHC-catalyzed
formal
[4+2]
cycloaddition
of
heterocyclic
alkenes
containing
polarized
double
bond
with
azolium-dienolate
intermediate
generated
from
α-bromo-α,β-unsaturated
aldehydes
without
external
oxidation
Breslow
intermediate.
Heterocyclic
cyclohexenones
were
produced
in
good
isolated
yields
(typically
about
90%)
stereochemical
outcomes
dr
>
20/1,
and
70-99%
ee).
synthetic
utility
the
protocol
was
exemplified
by
scope
alkenes.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(6), P. 4067 - 4073
Published: Feb. 23, 2024
We
describe
herein
an
N-heterocyclic-carbene-catalyzed
atroposelective
synthesis
of
axially
chiral
diaryl
ethers.
Through
a
sequentially
enantioselective
desymmetric
process
and
kinetic
resolution
process,
the
products
could
be
constructed
in
good
yields
with
excellent
enantiopurities.
Both
alcohols
phenols
were
compatible
this
catalytic
system.
The
carboxylic
acids
derived
from
esters
proven
to
potential
ligands
for
asymmetric
synthesis,
example,
Rh(III)-catalyzed
C–H
functionalization.
The Chemical Record,
Journal Year:
2023,
Volume and Issue:
23(7)
Published: March 21, 2023
Abstract
N
‐Heterocyclic
carbene
(NHC)
organocatalysis
has
emerged
as
a
powerful
tool
in
the
field
of
modern
organic
synthesis
especially
asymmetric
construction
various
cyclic
skeletons.
As
an
emerging
NHC‐bound
1,3‐bielectrophilic
intermediate,
alkynyl
acylazolium
drawn
substantial
attention
recent
years,
and
been
used
versatile
3C‐synthon
synthesizing
valuable
molecules
since
its
discovery.
In
this
review,
focused
on
different
pathways
for
formation
acylazoliums
from
precursors
like
alkynoic
esters,
acids
ynals,
advances
transformations
applications
pioneered
or
developed
over
last
decade
under
NHC‐catalysis
were
summarized
comprehensively.
At
same
time,
outlook
further
investigation
exploration
novel
reaction
modes
future
was
also
discussed.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(48)
Published: Oct. 11, 2023
Abstract
N
‐Heterocyclic
carbene
(NHC)
catalyzed
radical‐radical
reactions
have
been
proven
to
be
powerful
strategies
for
assembling
ketyl‐containing
compounds
via
single
electron
transfer
(SET)
pathway
under
either
thermal
conditions
or
photoredox
conditions.
In
this
context,
acylation
of
alkenes
radical
relay
NHC‐organocatalysis
has
also
opened
a
new
window
the
difunctionalization
construct
valuable
molecules
in
organic
synthesis.
review,
advances
and
progress
were
summarized
according
different
ways
generation
key
NHC‐bound
ketyl‐type
radicals.
Furthermore,
reaction
scopes,
limitations
mechanisms
discussed
based
on
types
catalytic
systems.
Conclusions
perspectives
put
forward
at
end.
The Chemical Record,
Journal Year:
2023,
Volume and Issue:
23(7)
Published: Jan. 26, 2023
Abstract
Over
the
last
ten
years,
combination
of
organocatalysis
with
transition
metal
(TM)
catalysis
has
become
one
most
important
toolboxes
used
for
synthesizing
optically
pure
compounds
containing
chiral
quaternary
centers,
including
spiro
heterocyclic
molecules.
The
dominant
method
in
enantioselective
synthesis
based
on
synergistic
includes
aminocatalysis
and
NHC
catalysis,
as
already
established
covalent
organocatalytic
strategies.
Another
area
widely
combined
TM
producing
enantiomerically
enriched
is
non‐covalent
dominated
by
phosphoric
acids,
thiourea,
squaramide
derivatives.
This
review
article
aims
to
summarize
methods
constructing
spirocyclic
heterocycles
a
catalysis.
Chemistry - An Asian Journal,
Journal Year:
2024,
Volume and Issue:
19(9)
Published: March 7, 2024
N-Heterocyclic
carbenes
(NHCs)
catalysts
have
been
employed
as
effective
tools
in
the
development
of
various
reactions,
which
made
notable
contributions
developing
diverse
reaction
modes
and
generating
significant
functionalized
molecules.
This
review
provides
an
overview
recent
advancements
chemo-
regioselective
activation
different
aldehydes
using
NHCs,
categorized
into
five
parts
based
on
modes.
A
brief
conclusion
outlook
is
provided
to
stimulate
novel
for
accessing
functional
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(17), P. 3552 - 3556
Published: April 19, 2024
A
formal
[3
+
2]
annulation
of
cyclohexadienone-tethered
ynals
is
enabled
by
an
N-heterocyclic
carbene
(NHC)
catalyst,
affording
a
tricyclo[6.2.1.04,11]undecane
framework.
This
study
represents
the
first
demonstration
using
C═C
double
bonds
as
reaction
partner
in
NHC-catalyzed
ynals.
strategy
characterized
mild
conditions
and
100%
atom
economy
well
high
catalytic
performance
efficiency.
Asian Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 3, 2025
Abstract
NHC‐Catalyzed
enantioselective
conversion
of
ynals
remains
challenging
through
nucleophilic
NHC‐allenolate
intermediates.
Herein,
we
present
an
NHC‐catalyzed
highly
asymmetric
intramolecular
[3+2]
annulation
cyclohexadienone‐tethered
ynals.
This
reaction
enables
a
rapid
and
efficient
construction
6,5,5‐tricyclic
frameworks
bearing
three
contiguous
stereocenters
in
excellent
enantioselectivities.
Additionally,
the
synthetic
utility
is
elaborated
gram‐scale
experiment
several
downstream
transformations.
Asian Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 8, 2025
Abstract
We
have
developed
an
N
‐heterocyclic
carbene
(NHC)‐catalyzed
[3+3]
annulation
of
α,β−γ,δ‐unsaturated
aldehydes
with
enamines
for
the
asymmetric
synthesis
dihydropyridinone
that
bearing
all‐carbon
quaternary
center.
This
strategy
proceeding
via
NHC‐mediated
γ,δ–protonation
α,β−γ,δ−unsaturated
aldehydes,
followed
by
cycloadditions.
protocol
delivers
a
wide
range
substituited
dihydropyridinones
in
good
yields
excellent
enantioselectivities.
