Molecules,
Journal Year:
2023,
Volume and Issue:
28(14), P. 5529 - 5529
Published: July 20, 2023
An
unprecedented
N-alkylation
of
3-nitroindoles
with
para-quinone
methides
was
developed
for
the
first
time.
Using
potassium
carbonate
as
base,
a
wide
range
structurally
diverse
N-diarylmethylindole
derivatives
were
obtained
moderated
to
good
yields
via
protection
group
migration/aza-1,6-Michael
addition
sequences.
The
reaction
process
also
demonstrated
by
control
experiments.
Different
from
previous
advances
where
3-nitrodoles
served
electrophiles
trapping
various
nucleophiles,
herein
is
featured
that
defined
latent
N-centered
nucleophiles
react
ortho-hydrophenyl
p-QMs
construction
N-diarylmethylindoles.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1824 - 1842
Published: Jan. 1, 2024
In
this
review,
we
briefly
summarize
the
recent
research
progress
in
enantioselective
higher-order
cycloadditions,
focusing
on
preparation
of
medium-sized
and
multicyclic
chiral
molecules
by
metal-free
catalysis.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(22), P. 4643 - 4647
Published: May 29, 2024
A
de
novo
method
for
direct
construction
of
cyclopenta[b]indolines
via
a
photocatalytic
fluoroalkylative
radical
cyclization
cascade
ynamides
has
been
established,
which
proceeds
sequence
addition,
1,5-HAT,
5-endo-trig
cyclization,
intramolecular
arylation,
and
oxidative
deprotonation.
This
protocol
allows
the
controllable
assembly
tricyclic
architecture
with
three
contiguous
stereocenters,
showcasing
its
high
efficiency,
compatibility,
regio-
diastereoselectivity
accessing
pharmacologically
significant
fluoroalkylated
cyclopenta[b]indolines.
It
represents
one
very
few
examples
tetrafunctionalization
alkynes.
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.
RSC Advances,
Journal Year:
2024,
Volume and Issue:
14(9), P. 6339 - 6359
Published: Jan. 1, 2024
This
review
provides
a
comprehensive
overview
of
the
significance
aurone
cores
in
organic
chemistry,
highlighting
their
crucial
role
as
synthetic
intermediates.
With
innate
electrophilic
reactivity
and
convenient
accessibility,
play
vital
catalysing
development
novel
methodologies
facilitating
creation
intricate
compounds.
The
objective
this
is
to
present
current
insightful
compilation
that
summarizes
progress
transformations,
focusing
on
diverse
cycloaddition
([3
+
2],
[4
3],
[10
2])
annulation
reactions.
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.
Chemistry - A European Journal,
Journal Year:
2024,
Volume and Issue:
30(34)
Published: April 15, 2024
Dearomative
Diels-Alder
cycloadditions
between
nitroarenes
and
2-trimethylsilyloxycyclohexadiene
are
carried
out
under
high
pressure
at
room
temperature
in
the
absence
of
any
chemical
promoter.
Reactions
performed
with
different
arenes,
including
highly
aromatic
naphthalenes
quinolines.
They
lead
to
3D-scaffolds
exquisite
exo-diastereoselectivity.
The
exo
approach
is
characterized
by
lower
distortion
substrates
a
late
TS
more
favorable
orbital
interactions
presumably
nitro
group
dienic
part,
explaining
stereoselectivity.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(33), P. 6681 - 6686
Published: Jan. 1, 2023
We
report
a
base-promoted
cyclization
with
indene-dienes
as
two
carbon
building
blocks
toward
diverse
spirocyclic
indene
scaffolds
including
hexacyclic
spiroindenes
bearing
benzo
pyran
motifs
and
pentacyclic
containing
oxindole
units
in
high
yields
excellent
diastereoselectivities.
