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.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(9), С. 5804 - 5816
Опубликована: Апрель 27, 2022
An
efficient
Cu-catalyzed
annulation
reaction
of
ketone
oxime
acetates
with
ortho-trifluoroacetyl
anilines
has
been
disclosed.
With
the
developed
protocol,
a
series
4-trifluoromethyl
quinolines
were
obtained
in
good
to
excellent
yields
(58-99%)
under
redox-neutral
conditions.
The
protocol
also
could
be
extended
ferrocene-based
for
construction
ferrocene-substituted
fluorine-containing
quinolines.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(12), С. 3322 - 3327
Опубликована: Янв. 1, 2022
The
higher-order
[10
+
2]
cycloaddition
of
3-nitroindoles
and
2-alkylidene-1-indanones
enables
the
dearomatization
affords
a
range
structurally
diverse
cyclopenta[
b
]indolines
with
excellent
results.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 5, 2025
Enantioselective
functionalization
of
4-aminoindoles
at
the
site-specific
C7
position
via
a
chiral
phosphoric
acid-catalyzed
Friedel-Crafts
reaction
with
cyclic
thioimidates
was
developed.
This
approach
enables
formation
4,7-difunctionalized
indoles
incorporating
N,S-acetal
motif
excellent
yield
and
enantioselectivity
(up
to
99%
>99%
ee).
The
protocol
is
also
compatible
isatin-derived
ketoimines
for
highly
enantioselective
synthesis
indole
derivatives
bearing
aza-quaternary
carbon
position.
synthetic
potential
demonstrated
by
gram-scale
experiments
versatile
transformations
products,
method
characterized
low
catalyst
loading,
site
specificity,
enantioselectivity,
broad
substrate
scope.
Abstract
Chiral
dispyrindolinone‐pyrrolidine‐indolinones
were
obtained
using
a
four‐step
synthetic
sequence:
(1)
preparation
of
thioureas
and
5‐arylidene‐thiohydantoins
from
(
R
)
or
S
)‐1‐(2,4‐dimethoxyphenyl)ethylamine;
(2)
1,3‐cycloaddition
reaction
the
chiral
with
azomethine
ylide
to
obtain
diastereomers'
mixture;
(3)
diastereomers
separation
removing
auxiliary
1‐(2,4‐dimethoxyphenyl)ethyl
group.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(5), С. 2520 - 2531
Опубликована: Янв. 27, 2022
In
this
study,
we
reported
a
hydrogen-bond-donor-directed
enantiodivergent
vinylogous
aldol-cyclization
cascade
reaction
of
3-alkylidene
oxindoles
with
isatins
and
o-quinones.
Both
enantiomers
can
be
prepared
by
thiourea
or
squaramide
cinchona
alkaloid
bifunctional
organocatalysts
the
same
quinine
scaffold.
Kinetic
study
data
provided
possible
mechanism
for
reaction.
The
DFT
calculation
showed
geometry
generated
dienolates
from
pronucleophiles
dominated
observed
switch
enantioselectivity.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
88(12), С. 7641 - 7650
Опубликована: Авг. 12, 2022
A
series
of
compounds
featuring
a
novel
bispiro[indanedione-oxindole-cyclopropane]
moiety
have
been
synthesized
through
squaramide-catalyzed
[2+1]
cycloaddition
reaction.
The
tandem
Michael-alkylation
reaction
2-arylidene-1,3-indanediones
with
3-bromooxindoles
furnished
the
cycloadducts
in
high
yields
excellent
diastereo-
and
enantioselectivities.
ammonium
ylide
catalytic
process,
as
key
intermediate,
was
revealed
by
high-resolution
mass
spectrometry
study.
Organic Letters,
Год журнала:
2023,
Номер
25(44), С. 8027 - 8032
Опубликована: Ноя. 2, 2023
An
organocatalytic
asymmetric
[3
+
2]
cycloaddition
of
β-trifluoromethyl
enones
with
3-(N-2,2,2-trifluoroethyl)
benzothiophene
ketimines
and
2-(N-2,2,2-trifluoroethyl)
was
described
for
the
first
time.
A
wide
spectrum
vicinally
bis(trifluoromethyl)-substituted
spiro
pyrrolidine-benzothiophenones
were
obtained
excellent
stereocontrol
(all
cases
>20:1
dr
up
to
99%
ee).
The
highlight
this
work
is
extremely
high
efficiency
in
construction
spirocyclic
benzothiophenone
derivatives
possessing
a
pyrrolidine
moiety
four
contiguous
stereocenters.
Organic Letters,
Год журнала:
2022,
Номер
24(4), С. 1094 - 1099
Опубликована: Янв. 25, 2022
An
unprecedented
(3+1)
cyclization
of
α-nitrosostyrenes,
generated
in
situ
from
α-bromooximes,
and
N-tosyloxycarbamates
was
developed,
which
enables
the
synthesis
a
range
structurally
unique
hitherto
unexplored
2,3-dihydrodiazete
N-oxides
moderate
to
high
yields.
The
products
possess
highly
strained
four-membered
ring
structure
containing
two
nitrogen
atoms.
synthetic
applicability
also
demonstrated
by
many
important
conversions
diverse
nitrogen-containing
compounds.
Molecules,
Год журнала:
2023,
Номер
28(18), С. 6488 - 6488
Опубликована: Сен. 7, 2023
Multicomponent
reactions
(MCRs)
have
undoubtedly
emerged
as
the
most
indispensable
tool
for
organic
chemists
worldwide,
finding
extensive
utility
in
synthesis
of
intricate
natural
products,
heterocyclic
molecules
with
significant
bioactivity,
and
pharmaceutical
agents.
The
multicomponent
one-pot
1,3-dipolar
cycloaddition
reactions,
which
were
initially
conceptualized
by
Rolf
Huisgen
1960,
find
application
contemporary
chemistry.
In
terms
green
synthesis,
is
highly
favored
owing
to
its
numerous
advantages,
including
high
step-
atom-economies,
remarkable
product
diversity,
well
excellent
efficiency
diastereoselectivity.
Among
pieces
research,
fascinating
reaction
involves
utilization
azomethine
ylides
generated
from
isatins
amino
acids
that
can
be
captured
various
dipolarophiles.
This
approach
offers
a
efficient
convenient
method
constructing
spiro-pyrrolidine
oxindole
scaffolds,
are
crucial
building
blocks
biologically
active
molecules.
Consequently,
this
review
delves
deeper
into
dipolarophiles
utilized
over
past
six
years.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(9), С. 6027 - 6039
Опубликована: Апрель 17, 2024
In
this
study,
[1+2+2]
cyclization
of
tryptamine-derived
isocyanides
with
3-ylideneoxindoles
was
systematically
investigated.
A
series
structurally
complex
spiro-oxindole
derivatives
were
obtained.
Characteristic
dynamic
covalent
chemistry
observed
and
confirmed
by
experiments
density
functional
theory
calculation.
Through
the
regulation
solvent,
temperature,
time,
precise
stereodivergent
synthesis
spiro-oxindoles
achieved.
