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.
ACS Central Science,
Journal Year:
2021,
Volume and Issue:
7(3), P. 432 - 444
Published: Feb. 22, 2021
Asymmetric
catalysis
has
been
recognized
as
the
most
enabling
strategy
for
accessing
chiral
molecules
in
enantioenriched
forms.
Catalytic
asymmetric
dearomatization
is
an
emerging
and
dynamic
research
subject
catalysis,
which
received
considerable
attention
recent
years.
The
direct
transformations
from
readily
available
aromatic
feedstocks
to
structurally
diverse
three-dimensional
polycyclic
make
catalytic
reactions
of
broad
interest
both
organic
synthesis
medicinal
chemistry.
However,
inherent
difficulty
disruption
aromaticity
demands
a
large
energy
input
during
process,
might
be
incompatible
with
conditions
generally
required
by
catalysis.
In
this
Outlook,
we
will
discuss
representative
strategies
examples
various
compounds
try
convince
readers
that
overcoming
above
obstacles,
could
advance
chemical
sciences
many
respects.
Chemical Reviews,
Journal Year:
2020,
Volume and Issue:
121(1), P. 110 - 139
Published: Aug. 6, 2020
In
this
review,
transition
metal-catalyzed
methodologies
and
applications
that
exploit
C–C
bond
cleavage
of
vinylcyclopropanes
(VCPs)
are
summarized
with
a
focus
on
cycloaddition
related
addition
reactions.
Transition
metals,
including
palladium,
nickel,
iron,
ruthenium,
rhodium,
cobalt,
iridium,
can
catalyze
the
bonds
in
activated
or
nonactivated
VCPs.
Additionally,
these
bond-breaking
reactions
occur
as
intra-
intermolecular
processes.
The
properties
VCPs
discussed
Introduction.
Various
involving
then
next
chapter.
cycloadditions
following
Finally,
challenges
potential
opportunities
outlined
last
Advanced Synthesis & Catalysis,
Journal Year:
2018,
Volume and Issue:
361(3), P. 405 - 425
Published: Aug. 20, 2018
Abstract
Fused
polycyclic
indoline
skeletons
are
found
in
many
natural
products
and
bioactive
molecules.
Several
approaches,
including
dearomative
cyclization
of
functionalized
indoles,
have
been
developed
for
the
rapid
synthesis
these
skeletons.
As
a
result
extensive
research
over
past
few
decades,
numerous
elegant
efficient
protocols
transition
metal‐catalyzed
indoles
to
afford
indolines
reported,
recent
developments
this
area
discussed
detail
review.
magnified
image
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
58(16), P. 5422 - 5426
Published: Feb. 12, 2019
Abstract
Over
the
past
years,
metal‐catalyzed
dearomative
cycloaddition
of
3‐nitroindoles
and
2‐nitrobenzofurans
have
emerged
as
a
powerful
protocol
to
construct
chiral
fused
heterocyclic
rings.
However,
organocatalytic
reaction
these
two
classes
heteroarenes
has
become
long‐standing
challenging
task.
Herein,
we
report
first
example
phosphine‐catalyzed
asymmetric
[3+2]‐cycloadditio
2‐nitrobenzofurans,
which
provide
new,
facile,
efficient
for
synthesis
2,3‐fused
cyclopentannulated
indolines
dihydrobenzofurans
by
reacting
with
allenoates
MBH
carbonates,
respectively
through
[3+2]‐cycloaddition.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
58(16), P. 5427 - 5431
Published: Feb. 16, 2019
Abstract
The
dearomatization
of
3‐nitroindoles
through
a
chiral‐phosphine‐mediated
[3+2]
annulation
reaction
is
described.
This
method
makes
use
readily
available
as
an
aromatic
feedstock
and
rapidly
delivers
wide
range
cyclopentaindoline
alkaloid
scaffolds
in
highly
enantioselective
manner.
Notably,
phosphine‐triggered
cyclization
has
not
been
utilized
previously
process.
Chinese Journal of Chemistry,
Journal Year:
2019,
Volume and Issue:
38(3), P. 287 - 294
Published: Dec. 12, 2019
When
“dark”
is
bright
:
the
scarcely
explored
electrophilic
profile
of
indolyl
core
(
dark‐side
)
continues
to
inspire
developments
in
organic
synthesis
by
means
new
catalytic
methodologies.
Recent
advancements
field
enabled
molecular
diversity
and
complexity
be
effectively
realized
within
heterocyclic
chemistry.
Journal of the American Chemical Society,
Journal Year:
2018,
Volume and Issue:
140(41), P. 13242 - 13252
Published: Sept. 21, 2018
A
three-component
coupling
using
lithiated
indoles,
boronate
esters
and
allylic
acetates
generates
chiral
indolines
with
adjacent
quaternary
stereocenters.
Successful
stereocontrol
required
the
use
of
phosphoramidite
ligands
not
previously
described
for
organopalladium
chemistry.
Mechanistic
studies
indicate
a
monodentate
PdL
intermediate,
stepwise
allylation-aryl/alkyl
migration.
protodeborylation
strategy
was
used
to
install
C–H
bond
in
place
C–B
bond.
photoredox
replace
C–C
highly
diastereoselective
manner.
In
specific
case
methyl-vinyl
ketone,
novel
radical-mediated
annulation
provides
polycyclic
products
high
enantio-
diastereoselectivity.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(3), P. 660 - 664
Published: Jan. 14, 2019
The
first
organocatalyzed
asymmetric
dearomative
cycloaddition
between
2-nitrobenzofurans
and
isatin-derived
Morita-Baylis-Hillman
carbonates
has
been
developed.
Using
a
modified
cinchona
alkaloid
as
the
catalyst,
series
of
structurally
diverse
cyclopenta[
b]benzofuran
derivatives
with
three
contiguous
stereocenters,
including
spiro-quaternary
chiral
center,
could
be
smoothly
obtained
in
excellent
results
(all
cases
>20:1
dr,
up
to
99%
yield
98%
ee).
utility
this
method
was
showcased
by
versatile
transformations
product.
Chemical Society Reviews,
Journal Year:
2021,
Volume and Issue:
50(10), P. 5985 - 6012
Published: Jan. 1, 2021
Pyrroloindolines
are
widely
present
in
natural
products.
In
this
review,
we
summarize
state-of-the-art
of
catalytic
asymmetric
synthesis
pyrroloindolines,
as
well
related
applications
to
products
total
synthesis.
