Molecules,
Journal Year:
2024,
Volume and Issue:
29(5), P. 1163 - 1163
Published: March 5, 2024
An
efficient
dearomative
(3
+
2)
cycloaddition
of
para-quinamines
and
2-nitrobenzofurans
has
been
developed.
This
reaction
proceeds
smoothly
under
mild
conditions
affords
a
series
benzofuro[3,2-b]indol-3-one
derivatives
in
good
to
excellent
yields
(up
98%)
with
perfect
diastereoselectivities
(all
cases
>
20:1
dr).
The
scale-up
synthesis
versatile
derivatizations
demonstrate
the
potential
synthetic
application
protocol.
A
plausible
mechanism
is
also
proposed
account
for
observed
process.
work
represents
first
instance
N-triggered
2-nitrobenzofurans.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(44), P. 8027 - 8032
Published: Nov. 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,
Journal Year:
2022,
Volume and Issue:
24(4), P. 1094 - 1099
Published: Jan. 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.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(7), P. 1373 - 1378
Published: Jan. 1, 2023
A
formal
[4
+
2]
cycloaddition
of
3-nitroindoles
with
ortho-aminophenyl
p-quinone
methides
via
a
dearomatization
process
was
developed.
This
method
provides
facile
approach
for
preparing
tetrahydro-5H-indolo[2,3-b]quinolones
good
results.
With
the
bifunctional
Cinchona
alkaloid-squaramide
as
catalyst,
asymmetric
version
reaction
successfully
afforded
corresponding
chiral
products
moderate
to
enantioselectivities.
work
represents
first
dearomative
electron-deficient
heteroarenes
triggered
by
aza-Michael
addition
from
p-QMs.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(8), P. 2121 - 2128
Published: Jan. 1, 2022
A
novel
asymmetric
[3
+
2]
cycloaddition
reaction
of
1,4-dipoles
and
nitroolefins
catalysed
by
the
cooperative
action
chiral
palladium/phosphine
complex
urea-tertiary
amine
is
described.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(11), P. 2149 - 2154
Published: March 16, 2022
The
diastereo-
and
enantioselective
dearomative
formal
[3
+
2]
cycloaddition
of
2-nitrobenzofurans
α-aryl-α-isocyanoacetate
esters
provides
tricyclic
compounds
bearing
the
3
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(22), P. 6172 - 6178
Published: Jan. 1, 2022
A
palladium-catalyzed
stereoselective
decarboxylative
allylation
of
azlactones
with
vinyl
methylene
cyclic
carbonates
affords
a
series
trisubstituted
allylic
amino
acid
derivatives
in
good
yields
an
exclusive
(
Z
)-configuration.
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.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(15), P. 10810 - 10817
Published: July 18, 2023
The
synthesis
of
3-thioether-substituted
dihydrofuro[2,3-b]benzofurans
involving
the
[3
+
2]
coupling
sulfur
ylides
with
2-nitrobenzofurans
has
been
realized
in
moderate
to
good
yields
under
mild
conditions
without
any
precious
catalysts
or
additives.
It
is
worth
mentioning
that
reutilization
departed
nitro-anion
reaction
process
facilitates
this
new
chemical
transformation
and
presents
a
manner
high
atom
economy
provide
products
complex
structure.
