Abstract
A
variety
of
structurally
diverse
spirocyclohexane
oxindoles
featuring
a
quaternary
carbon
centre
have
been
successfully
constructed
through
an
N‐heterocyclic
carbene‐catalyzed
[4+2]
annulation
isatin‐derived
enals
with
α
‐cyano‐
β
‐methylenones.
This
domino
process
exhibits
wide
substrate
tolerance,
operates
under
mild
conditions,
and
yields
products
high
enantioselectivities.
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:
2025,
Volume and Issue:
unknown
Published: Jan. 9, 2025
In
this
work,
we
developed
a
phosphine-catalyzed
cascade
lactonization/[2
+
1]
annulation
reaction
between
vinyl
oxiranes
and
sulfonium
compounds
for
the
highly
diastereoselective
construction
of
spiro-2(3H)-furanone
skeletons.
The
cycloaddition
proceeds
via
2(5H)-furanone
phosphonium
intermediate,
introducing
an
oxygen-containing
active
intermediate
phosphine
catalysis.
These
findings
highlight
significant
potential
harnessing
as
versatile
synthons
constructing
spirocyclic
through
simultaneous
multicyclic
skeleton
formation.
Arabian Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
17(8), P. 105845 - 105845
Published: May 23, 2024
Cyclopropenone
has
emerged
as
a
highly
versatile
precursor
in
organic
synthesis
due
to
its
diverse
reactivity.
The
cyclopropenone
derivatives
could
undergo
various
transformations
such
cycloaddition
reactions,
ring-opening
and
isomerization
reactions
the
presence
of
different
chemical
reagents.
Over
years,
significant
progress
been
made
manipulation
cyclopropenones
for
construction
carbocycles,
heterocycles,
other
useful
compounds.
Despite
several
reviews
that
have
concerned
chemistry
cyclopropenones,
utility
motifs
carbocycles
heterocycles
rarely
reported.
Herein,
we
report
recent
advancements
synthetic
precursors
towards
compounds
with
biological
significance.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(28)
Published: May 27, 2024
Abstract
A
straightforward
[3+2]
annulation
method
for
synthesizing
bisspiro(oxindole)
derivatives
has
been
developed
by
using
isatin‐derived
Morita‐Baylis‐Hillman
carbonates
and
p
‐quinone
methides
(
‐QMs)
with
4‐dimethylaminopyridine
(DMAP)
as
the
catalyst.
The
optimized
protocol
in
dichloromethane
(DCM)
solvent
achieves
good
yields
(up
to
87
%)
diastereoselectivity
(>20
:
1).
versatility
of
is
shown
through
synthesis
various
derivatives,
including
chiral
variants
up
82
%
ee.
intermediates
were
captured
HRMS,
a
plausible
reaction
pathway
was
proposed.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(43), P. 9322 - 9327
Published: Oct. 24, 2024
The
present
work
develops
a
DMAP-catalyzed
[3
+
2]
cycloaddition
of
vinyl
oxiranes
with
activated
ketone
compounds,
affording
dioxolane
derivatives
moderate
to
excellent
yields.
This
approach
represents
the
first
Lewis
base
(LB)-catalyzed
ring-opening
reaction
epoxides,
simultaneously
providing
rare
oxygen-containing
active
intermediate
in
this
field.
gram-scale
preparation
and
facile
derivatization
cycloadduct
highlight
significant
synthetic
potential
strategy.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(36), P. 7576 - 7583
Published: Sept. 3, 2024
An
efficient
pyridine-catalyzed
chemoselective
four-component
cascade
reaction
of
aromatic
aldehydes,
malononitrile/cyanoacetates,
Morita-Baylis-Hillman
(MBH)
carbonates,
and
alcohols
has
been
established.
This
one-pot
progressed
in
an
unusual
with
solvent
participation
via
a
Knoevenagel
condensation/oxa-Michael
addition/S
Chemical Science,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
Combined
experimental
and
quantum-chemical
studies
were
used
to
characterise
the
philicity/fugality
features
of
tertiary
phosphines
Michael
acceptors
in
phospha-Michael
reactions,
which
are
key
steps
phosphine-catalysed
organic
reactions.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 7, 2024
An
unexpected
phosphine-catalyzed
controllable
three-component
domino
reaction
involving
[1
+
2
2]
annulation
and
2]/[3
sequential
of
2-arylmethylidene
cyanoacetates/malononitriles
with
Morita-Baylis-Hillman
(MBH)
carbonates
has
been
developed.
A
broad
range
densely
functionalized
cyclopentanes
diquinanes
bearing
five
or
four
consecutive
stereogenic
centers,
including
two
all-carbon
quaternary
stereocenters,
were
smoothly
acquired
in
moderate
to
excellent
yields
under
mild
conditions
from
readily
available
materials.
Moreover,
this
divergent
transformation
enables
the
simultaneous
generation
three
new
C-C
bonds
one
carbocyclic
rings
only
step.
Molecules,
Journal Year:
2024,
Volume and Issue:
29(8), P. 1790 - 1790
Published: April 15, 2024
A
chemselective
catalyst-free
three-component
1,3-dipolar
cycloaddition
has
been
described.
The
unique
polycyclic
THPI
and
THIQs
were
creatively
employed
as
dipolarophiles,
which
led
to
the
formation
of
functionalized
β-tetrahydrocarboline-
tetrahydroisoquinoline-fused
spirooxindoles
in
60–94%
yields
with
excellent
diastereoselectivities
(10:
1−>99:
1
dr).
This
reaction
not
only
realizes
a
concise
THPI-
or
THIQs-based
cycloaddition,
but
also
provides
practical
strategy
for
construction
two
distinctive
spirooxindole
skeletons.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(38), P. 7817 - 7833
Published: Jan. 1, 2024
A
planar
chiral
[2.2]paracyclophane-based
phosphine-phenol
catalyst
catalyzed
the
(3
+
2)
annulation
reaction
of
ethyl
2,3-butadienoate
with
3-methyleneindolin-2-ones
to
produce
2,5-disubstituted
cyclopentene-fused
C3-spirooxindoles
in
high
yields
regio-,
diastereo-,
and
enantioselectivities.
This
was
suitable
for
reactions
not
only
benzylideneindolinones
but
also
alkylideneindolinones,
phosphine-catalyzed
which
have
yet
been
reported.
Density
functional
theory
calculations
suggested
that
formation
hydrogen
bonds
between
phenolic
OH
group
allenoate
carbonyl
group,
rather
than
indolinone,
contributed
an
efficient
space
at
enantiodetermining
step.
