ChemistrySelect,
Journal Year:
2024,
Volume and Issue:
9(3)
Published: Jan. 17, 2024
Abstract
Organic
synthesis
involves
the
production
of
important
chemical
structures
using
scalable
and
cost‐effective
methods
that
are
also
environmentally
friendly.
In
this
review,
a
detailed
analysis
use
iodine
DMSO
in
various
synthetic
routes
for
preparation
valuable
targets
presented.
These
reduce
acceptance
on
expensive
additives
reagents,
offer
more
sustainable
solution
these
scaffolds.
The Chemical Record,
Journal Year:
2019,
Volume and Issue:
20(6), P. 541 - 555
Published: Oct. 14, 2019
The
development
of
synthetic
protocols
to
access
architectures
with
broad
structural
and
functional
diversity
from
readily
available
starting
materials
is
very
attractive
in
both
organic
medicinal
chemistry
fields.
Toward
this
objective,
the
multifunctional
isatin-derived
Morita-Baylis-Hillman
(MBH)
adducts
provide
opportunities
construct
a
variety
complex
scaffolds
containing
"privileged"
oxindole
motif
through
several
catalytic
pathways.
By
forming
ammonium
or
phosphonium
salts
Lewis
bases,
MBH
can
undergo
allylic
substitutions
range
nucleophiles,
usually
SN
2'-SN
2'
pattern.
Besides,
assisted
by
Brønsted
corresponding
onium
be
converted
into
ylide
intermediates,
which
various
annulation
reactions
even
1,3-difunctionalizations.
Moreover,
recent
cooperative
catalysis
bases
transition
metal
complexes
further
puts
forward
application
adducts.
This
tutorial
review
covers
significant
transformations
adducts,
mostly
an
asymmetric
version,
catalyzed
over
past
decade.
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(14), P. 5536 - 5540
Published: Jan. 2, 2020
We
describe
herein
a
highly
diastereo-
and
enantioselective
[4+3]-cycloannulation
of
ortho-quinone
methides
carbonyl
ylides
to
furnish
functionalized
oxa-bridged
dibenzooxacines
with
excellent
yields
stereoselectivity
in
single
synthetic
step.
The
combination
rhodium
chiral
phosphoric
acid
catalysis
working
concert
generate
both
transient
intermediates
situ
provides
direct
access
complex
bicyclic
products
two
quaternary
one
tertiary
stereogenic
centers.
may
be
further
into
valuable
enantiomerically
enriched
building
blocks.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
58(42), P. 15021 - 15025
Published: Aug. 15, 2019
Abstract
Asymmetric
reactions
merging
organocatalysis
and
metal
catalysis
significantly
broaden
the
scope
of
organic
synthesis.
Nevertheless,
accomplishment
stereoselective
annulations
combining
two
types
dipole
species,
independently
generated
from
activations
organocatalysts
complexes,
still
remains
as
a
challenging
task.
Now,
Morita–Baylis–Hillman
carbonates
isatins
carbamate‐functionalized
allyl
could
be
chemoselectively
activated
by
achiral
Lewis
basic
tertiary
amines
chiral
iridium
complexes.
The
zwitterionic
allylic
ylides
1,4‐π‐allyliridium
dipoles
formed
in
situ
are
assembled
highly
[4+3]
annulation
pattern.
Similar
cooperative
catalytic
strategy
applied
for
vinyl
aziridines,
furnishing
an
asymmetric
[3+3]
reaction
also
with
excellent
stereocontrol.
Chemistry - An Asian Journal,
Journal Year:
2020,
Volume and Issue:
15(8), P. 1225 - 1233
Published: Feb. 27, 2020
The
spirooxindole
unit
is
one
of
the
most
widely
investigated
compound
skeletons
existing
in
numerous
natural
and
pharmaceutical
molecules.
Thus,
a
large
number
synthetic
methodologies
have
already
been
reported
to
construct
such
core
structure.
trifluoromethyl
group
another
privileged
organic
chemistry.
introduction
CF3
an
framework
can
significantly
improve
properties
molecule.
In
this
context,
efficient
approach
for
construction
trifluoromethyl-containing
spirooxindoles
becomes
promising
research
direction
among
communities
industry
academia.
Minireview,
recent
advances
summarized
discussed.
addition,
representative
corresponding
reaction
mechanisms
described
as
well.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(11), P. 4240 - 4244
Published: May 15, 2020
A
chiral
tertiary
amine-catalyzed
asymmetric
γ-regioselective
(4
+
3)
annulation
reaction
of
isatin-derived
Morita-Baylis-Hillman
carbonates
and
1-azadienes
was
developed,
delivering
azepane
spirooxindoles
with
excellent
stereoselectivity.
In
addition,
by
tuning
the
substituents
carbonates,
switchable
γ-(4
or
α-(4
1)
o-quinone
methides
observed
to
furnish
benzo[b]oxepines
2,3-dihydrobenzofurans,
respectively,
under
similar
catalytic
conditions.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(19), P. 5358 - 5382
Published: Jan. 1, 2022
In
this
review,
the
advances
made
over
last
6
years
in
[4
+
1]-annulation
reactions
involving
sulfonium,
sulfoxonium
and
ammonium
ylides,
as
well
diazo
compounds
carbenes
are
summarized.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(4), P. 1048 - 1055
Published: Jan. 1, 2022
An
asymmetric
organocatalytic
cascade
reaction
has
been
reported
for
the
rapid
assembly
of
multifunctionalized
α-carboline-spirooxindole
hybrids,
which
suppressed
proliferation
in
colorectal
cancer
cells.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(21), P. 8559 - 8564
Published: Oct. 26, 2021
We
report
asymmetric
[4
+
3]
annulations
between
isatin-derived
Morita–Baylis–Hillman
carbonates
and
two
types
of
vinyl
synergistically
catalyzed
by
tertiary
amines
transition
metals,
through
chemoselective
assemblies
in
situ
formed
allylic
ylides
metal-containing
1,4-dipoles.
A
range
oxepane
frameworks
are
generally
constructed
moderate
to
good
yields
with
high
stereocontrol.
Moreover,
all
four
diastereomers
for
the
products
bearing
vicinal
stereocenters
accessible
tuning
amine
metal
catalysts.
Organic Chemistry Frontiers,
Journal Year:
2021,
Volume and Issue:
8(21), P. 6032 - 6037
Published: Jan. 1, 2021
A
visible
light
photocatalyzed
or
metal-catalyzed
three-component
cyanoalkylsulfonylation
of
1-(allyloxy)-2-(1-arylvinyl)benzenes,
potassium
metabisulfite
and
cyclobutanone
oxime
esters
is
developed.
