Molecules,
Journal Year:
2023,
Volume and Issue:
28(6), P. 2765 - 2765
Published: March 19, 2023
Catalytic
asymmetric
dearomative
[3+2]
cycloaddition
of
α-imino
γ-lactones
with
either
3-nitroindoles
or
2-nitrobenzofurans
by
using
a
chiral
copper
complex
as
the
catalyst
was
developed.
A
wide
range
structurally
diverse
polyheterocyclic
compounds
containing
spirocyclic-fused
butyrolactone-pyrrolidine-indoline
and
butyrolactone-pyrrolidine-dihydrobenzofuran
skeletons
could
be
smoothly
obtained
excellent
results
(>99:1
dr
98%
ee).
The
potential
synthetic
applications
this
methodology
were
also
demonstrated
scale-up
experiment
transformations
one
product.
This
method
is
characterized
high
induction,
functional
group
tolerance
scalability,
attractive
product
diversification.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(25), P. 4603 - 4608
Published: June 15, 2022
A
copper-catalyzed
umpolung
of
N-2,2,2-trifluoroethylisatin
ketimines
for
the
enantioselective
1,3-dipolar
cycloaddition
with
benzo[b]thiophene
sulfones
was
developed.
Using
a
catalyst
system
consisting
an
(S,Sp)-tBu-Phosferrox
ligand,
Cu(OTf)2,
and
Cs2CO3,
range
pentacyclic
spirooxindoles
containing
pyrrolidine
benzo[b]sulfolane
subunits
were
obtained
in
high
efficiency
excellent
regio-,
diastereo-,
enantioselectivites
under
mild
conditions.
The
practicality
versatility
reaction
also
demonstrated.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(3), P. 826 - 831
Published: Jan. 14, 2022
We
disclose
a
Ag-catalyzed
asymmetric
interrupted
Barton–Zard
reaction
of
α-aryl-substituted
isocyanoacetates
with
2-
and
3-nitroindoles,
which
enables
the
dearomatization
nitroindoles
hence
offers
rapid
access
to
an
array
optically
active
tetrahydropyrrolo[3,4-b]indole
derivatives
bearing
three
contiguous
stereogenic
centers,
including
two
tetrasubstituted
chiral
carbon
atoms
pretty
outcomes
(up
99%
yield,
91:9
dr,
96%
ee).
The
synthetic
potential
protocol
was
showcased
by
gram-scale
versatile
transformations
product.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(22), P. 4052 - 4057
Published: May 27, 2022
With
a
Cu(OTf)2/chiral
ferrocenyl
P,N-ligand
complex
as
catalyst,
the
enantioselective
desymmetrization
of
N-arylmaleimides
was
successfully
realized
by
taking
advantage
asymmetric
1,3-dipolar
cycloaddition
reaction
N-2,2,2-trifluoroethylisatin
ketimines.
A
series
structurally
diverse
F3C-containing
octahydropyrrolo[3,4-c]pyrroles,
bearing
four
contiguous
carbon
stereocenters
and
one
stereogenic
chiral
C-N
axial
bond,
were
obtained
with
excellent
results
(≤99%
yield,
>20:1
dr,
99%
ee).
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3310 - 3315
Published: April 8, 2024
A
catalyst
system
consisting
of
a
chiral
phosphoramidite
ligand
and
Pd2(dba)3·CHCl3
causes
the
decarboxylation
5-vinyloxazolidine-2,4-diones
to
generate
amide-containing
aza-π-allylpalladium
1,3-dipole
intermediates,
which
are
capable
triggering
dearomatization
3-nitroindoles
for
diastereo-
enantioselective
[3+2]
cycloaddition,
leading
formation
series
highly
functionalized
pyrroloindolines
containing
three
contiguous
stereogenic
centers
with
excellent
results
(up
99%
yield,
88:12
dr,
96%
ee).
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(9), P. 6025 - 6037
Published: April 18, 2022
A
dearomatization
process
of
3-nitroindoles
enabled
using
palladium-catalyzed
decarboxylative
[4
+
2]
cycloaddition
either
2-alkylidenetrimethylene
carbonates
or
2-(hydroxymethyl)-3-arylallyl
has
been
developed,
affording
a
wide
range
indoline-fused
tetrahydropyrans
in
good
yields
with
excellent
diastereoselectivities.
This
reaction
features
substrate
scope
and
mild
conditions
represents
the
first
example
application
π-allyl
palladium
1,4-[O,C]-dipole
species
for
dearomative
electron-deficient
heteroarenes.
RSC Advances,
Journal Year:
2023,
Volume and Issue:
13(11), P. 7063 - 7075
Published: Jan. 1, 2023
Recent
updates
on
the
synthesis
of
CF
3
-containing
spirocyclic-oxindoles
by
employing
N
-2,2,2-trifluoroethylisatin
ketimines
are
described
in
this
review
article.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(11), P. 2648 - 2652
Published: Jan. 1, 2023
Herein,
we
disclose
the
first
Pd-catalyzed
enantioselective
(4
+
3)
cycloaddition
of
N
-2,2,2-trifluoroethylisatin
ketimines
with
2-methylidenetrimethylene
carbonate.
European Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
2022(18)
Published: April 5, 2022
Abstract
Dearomatization
reactions
employing
simple
aromatic
compounds
have
showcased
remarkable
progress
in
the
recent
decade
and
emerged
as
one
of
most
straightforward
powerful
tools
for
creation
highly
functionalized,
three‐dimensional
molecular
frameworks
commonly
encountered
medicinal
chemistry
life
sciences.
Among
use,
nitro(hetero)arenes,
which
feature
a
less
pronounced
character
due
to
presence
electron‐withdrawing
nitro
group,
been
extensively
used
different
types
dearomatization
reactions.
The
dearomative
annulation
reaction
serves
versatile
method
construction
complex
polycyclic
systems.
This
overview
presents
brief
summary
impressive
advances
nitro(hetero)arenes
provides
some
inspirations
future
research.
Chirality,
Journal Year:
2022,
Volume and Issue:
34(7), P. 1019 - 1034
Published: May 6, 2022
Abstract
A
readily
available
chiral
cyclohexanediamine‐derived
bifunctional
tertiary
amine‐squaramide
catalyst
is
more
effective
for
the
asymmetric
dearomative
1,3‐dipolar
cycloaddition
of
2‐nitrobenzofurans
and
N
‐2,2,2‐trifluoroethylisatin
ketimines.
range
structurally
diverse
spiro‐fused
polyheterocyclic
compounds
containing
oxindole,
pyrrolidine,
hydrobenzofuran
motifs
were
smoothly
obtained
in
excellent
results
(up
to
99%
yield,
>20:1
dr
all
cases
up
ee).
This
method
features
high
efficiency,
mild
reaction
conditions,
exquisite
induction,
wide
functional
group
tolerance,
great
potential
scale‐up
synthesis,
attractive
product
diversification.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(13), P. 2623 - 2628
Published: March 24, 2024
An
efficient
dearomative
cyclization
of
2-nitrobenzofurans
via
a
thiol-triggered
tandem
Michael
addition/intramolecular
Henry
reaction
has
been
developed.
A
range
thiochromeno[3,2-b]benzofuran-11-ols
and
tetrahydrothieno[3,2-b]benzofuran-3-ols
could
be
obtained
in
up
to
99%
yield
>20:1
dr.
The
valuable
thiochromone
fused
benzofurans
prepared
with
the
2-mercaptobenzaldehyde
reaction/rearomatization/oxidative
dehydrogenation
process
one-pot
two-step
operation.
mechanism
for
was
tentatively
proposed.
