Molecules,
Год журнала:
2023,
Номер
28(6), С. 2765 - 2765
Опубликована: Март 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,
Год журнала:
2024,
Номер
26(8), С. 1589 - 1594
Опубликована: Фев. 22, 2024
This
study
demonstrates
a
highly
efficient
regiodivergent
ligand-controlled
palladium-catalyzed
cycloaddition
reaction
of
vinyloxazolidine-2,4-diones
with
1,3,5-triazinanes.
In
the
presence
diphosphine
ligand,
proceeds
via
(5+2)
pathway
to
afford
1,3-diazepin-4-ones
in
excellent
yields,
while
using
monophosphine
smoothly
(3+2)
give
imidazolidin-4-ones
good
yields.
European Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 2, 2025
Abstract
This
review
collects
the
recent
developments
in
synthesis
of
chiral
heterocycles
through
enantioselective
silver‐catalyzed
transformations
published
since
2018.
It
demonstrates
power
silver
catalysts
as
special
mild
Lewis
acids
to
provide
an
impressive
diversity
reaction
pathways,
such
1,3‐dipolar
cycloadditions,
various
types
cyclizations,
along
with
a
wide
variety
more
complex
domino/tandem
reactions,
allowing
many
novel
heterocyclic
products
be
achieved
high
enantioselectivities.
We
report
the
first
example
of
dearomative
(3
+
2)
cycloadditions
3-nitro(aza)-indole,
-benzofuran,
and
-benzothiophene
derivatives
in
presence
allenyl
sulfones,
using
sulfinate
ammonium
ion
pairs
as
organocatalytic
promoters.
The
methodology
provides
a
new,
facile,
efficient
protocol
for
synthesis
functionalized
2,3-fused
cyclopentannulated
indolines
dihydrobenzofurans.
Organic Letters,
Год журнала:
2022,
Номер
24(45), С. 8348 - 8353
Опубликована: Ноя. 10, 2022
A
palladium-catalyzed
enantioselective
α-allylation
of
deconjugated
butenolides
with
aza-π-allylpalladium
1,4-diploes,
in
situ
generated
from
palladium-mediated
decarboxylation
cyclic
carbamates
and
amide-substituted
acyclic
carbonates,
has
been
successfully
developed.
An
array
enantioenriched
2-piperidones
bearing
an
all-carbon
quaternary
stereocenter
were
obtained
high
yields
excellent
enantioselectivities
(up
to
99%
yield
ee).
The
utility
this
method
was
also
showcased
by
a
large-scale
reaction
synthetic
transformations
the
product.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(5), С. 620 - 681
Опубликована: Янв. 17, 2023
Abstract
This
review
updates
the
field
of
enantioselective
domino
reactions
promoted
by
chiral
catalysts
derived
from
noble
metals,
including
palladium,
silver,
rhodium,
ruthenium,
iridium
and
gold,
published
since
beginning
2019.
It
illustrates
how
much
a
diversity
these
allow
unprecedented
asymmetric
many
types
to
be
achieved
with
excellent
enantioselectivity,
giving
direct
access
wide
variety
complex
molecules.
magnified
image
Organic Letters,
Год журнала:
2024,
Номер
26(15), С. 3310 - 3315
Опубликована: Апрель 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,
Год журнала:
2022,
Номер
87(9), С. 6025 - 6037
Опубликована: Апрель 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.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(21), С. 4332 - 4357
Опубликована: Янв. 1, 2023
Silver
catalysis
offers
environmentally
friendly
and
simple
protocols
to
construct
N-heterocycles.
Inspired
by
its
appeal,
herein
we
have
summarized
developments
in
the
silver-catalyzed
synthesis
of
N-heterocycles
since
2019.
Organic Letters,
Год журнала:
2024,
Номер
26(13), С. 2623 - 2628
Опубликована: Март 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.
