Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(59)
Published: Aug. 7, 2023
An
unprecedented
enantioselective
organocatalytic
spirocyclization
strategy
is
presented
by
in
situ
generation
of
aminoisobezofulvenes.
The
reaction
sequence
involves
a
reductive
Michael/aldol-condensation/Michael
addition
cascade
iminium-enamine
catalysis.
key
success
this
was
the
formation
intermediatory
nucleophilic
aminoisobenzofuvenes
accountable
for
intramolecular
Michael
addition.
Benzospirononanes
featuring
an
all
carbon
qauternary
spirocenter
were
obtained
using
proline-derived
amino-organocatalyst
moderate
to
good
yields
and
excellent
diastereo-
enantioselectivities
(up
>20
:
1
dr,
99
%
ee).
Post-methodological
manipulation
benzospirononanes
also
demonstrated.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(16), P. 11562 - 11580
Published: July 27, 2023
Diverse
functionalized
dihydrobenzofuran
spiro-indanedione-oxindole
scaffolds
were
conveniently
synthesized
by
base-promoted
cyclization
reaction
of
Morita-Baylis-Hillman
(MBH)
carbonates
isatins
and
2-(o-hydroxybenzylidene)-1,3-indanediones.
The
two
diastereomeric
dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines]
could
be
selectively
using
DABCO
or
DMAP
as
a
base
promoter.
More
importantly,
facilitated
the
annulation
MBH
formates
2-(o-hydroxybenzylidene)-1,3-indanediones
selectively,
resulting
in
spiro[cyclopropa[c]chromene-1,2'-indene]-1',3'-diones
dispiro[indene-2,1'-cyclopenta[b]benzofuran-2',3″'-indolines].
Additionally,
similar
with
maleimides
afforded
dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-c]pyrrole-4',3″'-indolines]
high
yields
diastereoselectivity.
Sustainable Chemistry for the Environment,
Journal Year:
2024,
Volume and Issue:
5, P. 100066 - 100066
Published: Jan. 6, 2024
The
one-pot,
three-component
cyclization
reaction
a
wide
variety
of
aryl/heteroaryl
aldehydes,
hydroxylamine
hydrochloride,
and
β-keto
ester
compounds
was
performed
in
simple
manner.
reactions
carried
out
the
presence
sodium
chloride
(NaCl)
as
profitable,
green,
efficient
catalyst
at
room
temperature.
Optimization
experiments
indicate
that
amount
17
mol%
loaded
NaCl
is
sufficient
to
catalyze
reaction.
Among
advantages
this
NaCl-catalyzed
method
are
availability
catalyst,
no
need
for
synthesis
several
steps,
commercially
available
reactants,
use
aqueous
conditions,
clean
synthesis,
non-inflammable
medium,
environmental
pollution,
safety,
cost-effectiveness,
pot-economy,
optimum
efficiency,
carbon
economy
steps.
Due
absence
harmful
solvents,
an
abundant,
low-cost,
useful
water
solvent,
considered
green
synthesis.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(24), P. 4412 - 4439
Published: Nov. 16, 2023
Abstract
Spirooxindoles
are
privileged
scaffolds
in
diverse
bioactive
natural
products
and
pharmaceuticals,
significant
achievements
for
the
construction
of
these
molecules
have
thus
been
made
past
years.
Among
them,
organocatalysis,
particular,
nucleophilic
Lewis
base
catalysis,
has
recently
emerged
as
an
efficient
reliable
method
preparation
valuable
functionalized
spirooxindoles.
According
to
different
kinds
catalysts,
we
summarize
classify
three
catalytic
strategies;
tertiary
amine‐catalyzed
cycloadditions,
NHC‐catalyzed
phosphine‐catalyzed
respectively.
Through
methods,
potential
spirooxindole
skeletons
owning
various
functional
groups
can
be
produced
enrich
small
organic
molecule
library.
In
this
review,
describe
a
comprehensive
updated
advances
cycloaddition
reactions
Meanwhile,
related
mechanism
application
annulation
strategies
product
total
synthesis
will
highlighted
detail.
Scientific Reports,
Journal Year:
2025,
Volume and Issue:
15(1)
Published: April 30, 2025
The
present
investigation
has
introduced
a
new
class
of
isocyanide/acetylene-based
multicomponent
reactions
(IAMCRs).
These
are
robust
technique
for
efficiently
synthesizing
intricate
spiro
architectures
through
zwitterionic
adduct.
coupling
reaction
between
the
"in
situ"
generated
dipoles
isocyanide-acetylenic
ester
adducts
and
3-alkyl-4-arylidene-isoxazol-5(4H)-one
derivative
presents
highly
effective
synthetic
pathway
obtaining
novel
1-oxo-2-oxa-3-azaspiro[4.4]nona-3,6,8-triene
heterocycles.
broad
range
substrates,
standard
experimental
conditions,
straightforward
procedure,
impressive
yields
make
our
catalyst-free
three-component
approach
practical
green,
as
it
remarkably
offers
step-,
time-
cost-effectiveness
based
on
green
metrics.
New Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
47(35), P. 16636 - 16642
Published: Jan. 1, 2023
A
general
mechanistic
map
of
the
PPh
3
-catalyzed
transformation
reaction
MBH
carbonate
has
been
theoretically
studied
and
NCI
ELF
analyses
are
performed
to
disclose
origins
selectivities
role
catalyst,
respectively.
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.
ChemistrySelect,
Journal Year:
2023,
Volume and Issue:
8(39)
Published: Oct. 19, 2023
Abstract
DABCO
promoted
one‐pot
three‐component
reaction
of
aromatic
amines,
dialkyl
but‐2‐ynedioates
and
MBH
nitriles
isatins
selectively
afforded
two
diastereomeric
spiro[indoline‐3,4′‐pyridines]
in
comparable
yields.
On
the
other
hand,
cyclization
carbonates
DCM
at
room
temperature
gave
spiro[cyclopentane‐1,3′‐indoline]
derivatives,
while
chloroform
70
°C
resulted
unique
cyclopenta[
c
]quinolone
derivatives
with
ring‐opening
isatin
moiety.
A
plausible
mechanism
was
rationally
proposed
to
explain
formation
different
products.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(25)
Published: April 8, 2024
Abstract
A
catalytic
asymmetric
(3+2)
cyclization
of
pyrazolone‐based
MBH
adducts
with
alkylidenyl
isoxazolones
was
presented
by
using
DMAP‐derived
chiral
catalyst,
affording
bis‐spirocyclic
pyrazolones
bearing
vicinal
all‐carbon
quaternary
stereocenters
within
an
imbedded
cyclopentene
ring
scaffold
in
good
yields
excellent
stereoselectivities
under
mild
conditions.
