Stereodivergent Construction of 3,3′-Disubstituted Oxindoles via One-Pot Sequential Allylation/Alkylation and Its Application to the Total Synthesis of Trigolute B and D
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 27, 2025
The
absolute
and
relative
configurations
of
bioactive
chiral
molecules
are
typically
relevant
to
their
biological
properties.
It
is
thus
highly
important
desirable
construct
all
possible
stereoisomers
a
lead
candidate
or
given
natural
compound.
Synergistic
dual
catalysis
has
been
recognized
as
reliable
synthetic
strategy
for
variety
predictable
stereodivergent
transformations.
Despite
the
impressive
progress
made
in
this
field,
carbon-carbon
bond-formation
reactions
involving
stabilized
nucleophiles
remain
elusive.
Herein,
we
report
an
iridium-
magnesium-catalyzed
one-pot
sequential
allylic
alkylation/nucleophilic
alkylation
cascade
process
synthesis
four
3,3'-disubstituted
oxindoles
through
three-component
reaction.
A
diverse
array
products
readily
prepared
with
high
functional
group
compatibility
good
yields
excellent
diastereo-
enantioselectivities.
Subsequently,
total
spirooxindole
alkaloid
trigolutes
B
D
accomplished
concise
unified
route
using
same
set
starting
materials.
Язык: Английский
Copper-Catalyzed Remote Asymmetric Yne-Allylic Substitution of Yne-Allylic Esters with Anthrones
Organic Letters,
Год журнала:
2024,
Номер
26(27), С. 5758 - 5763
Опубликована: Июль 1, 2024
Anthrones
are
key
structural
motifs
in
many
natural
products
and
pharmaceutical
chemicals.
However,
due
to
its
unique
tricyclic
aromatic
structure,
the
synthetic
space
for
development
of
chiral
anthrone
derivatives
is
largely
limited.
By
utilizing
potential
copper-catalyzed
remote
asymmetric
yne-allylic
substitution
reaction,
we
describe
first
example
highly
regio-
enantioselective
on
various
esters
with
anthrones
under
a
mild
reaction
condition,
which
afforded
range
enantioenriched
1,3-enynes
exhibiting
broad
functional
group
tolerance
across
51
examples.
Язык: Английский
Chalcogen Modification: One-Step Strategy for Tuning the Photophysical Properties and NIR Phototherapy of Iodinated BODIPY
Materials Chemistry Frontiers,
Год журнала:
2024,
Номер
8(20), С. 3308 - 3320
Опубликована: Янв. 1, 2024
A
schematic
illustration
of
iodinated
BODIPY
based
on
chalcogen
modification
the
photophysical
properties
for
near-infrared
phototherapy
tumors.
Язык: Английский
Palladium-Catalyzed Enantioselective Intramolecular Heck Reaction to Access Chiral C3-Tertiary Indolines
ACS Catalysis,
Год журнала:
2025,
Номер
unknown, С. 7191 - 7200
Опубликована: Апрель 17, 2025
Язык: Английский
Ni/Cu Dual‐Catalyzed Propargylation for the Stereodivergent Synthesis of Methohexital
Advanced Science,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 25, 2024
The
development
of
efficient
methodologies
for
the
controlled
manufacture
specific
stereoisomers
bearing
quaternary
stereocenters
has
prompted
advances
in
a
variety
scientific
disciplines
including
pharmaceutical
chemistry,
materials
science,
and
chemical
biology.
However,
complete
control
absolute
relative
stereochemical
configurations
alkyne
derivatives
remains
an
unmet
synthetic
challenge.
Herein,
Ni/Cu
dual-catalyzed
asymmetric
propargylic
substitution
reaction
is
presented
to
produce
propargylated
products
with
all-carbon
high
yields
significant
diastereo-
enantioselectivities
(up
>20:1
dr,
>99%
ee).
synthesis
all
variants
methohexital,
widely
used
sedative-hypnotic
drug,
exemplifies
efficacy
stereodivergent
propargylation.
Язык: Английский
Diarenofuran[b]-fused BODIPYs: One-Pot SNAr-Suzuki Synthesis and Properties
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 15, 2024
We
present
a
streamlined
methodology
that
integrates
regioselective
tetrahalogen-BODIPY
and
Язык: Английский
Multifunctionalization of Alkenyl Alcohols via a Sequential Relay Process
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
146(45), С. 30733 - 30740
Опубликована: Окт. 29, 2024
Aryl-substituted
aliphatic
amines
are
widely
recognized
as
immensely
valuable
molecules.
Consequently,
the
development
of
practical
strategies
for
construction
these
molecules
becomes
increasingly
urgent
and
critical.
Here,
we
have
successfully
achieved
multifunctionalization
reactions
alkenyl
alcohols
in
a
sequential
relay
process,
which
enables
transformation
patterns
arylamination,
deuterated
methylenated
arylamination
to
easy
access
multifarious
arylalkylamines.
Notably,
novel
functionalization
mode
carbonyl
groups
has
been
developed
facilitate
processes
deuterium
incorporation
methylene
introduction,
thereby
providing
new
means
diverse
transformations
groups.
This
methodology
displays
wide
tolerance
toward
functional
groups,
while
also
exhibiting
good
applicability
across
various
skeletal
structures
alkenols
amines.
Язык: Английский
Pd/Cu-Cocatalyzed Asymmetric Cascade Heck/Tsuji–Trost Reaction to Access Non-natural Tryptophans
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 20, 2024
A
Pd-catalyzed
asymmetric
Heck
cascade
reaction
involving
the
intramolecular
carbopalladation
of
unsaturated
hydrocarbons,
followed
by
nucleophilic
trapping
resulting
palladium
species,
is
a
powerful
approach
for
constructing
chiral
N-heterocycles.
However,
use
prochiral
nucleophiles
in
these
reactions
remains
significantly
underexplored.
Herein,
we
report
novel
Pd/Cu
catalytic
system
Heck/Tsuji–Trost
allenamides
and
aldimine
esters.
This
robust
method
allows
rapid
synthesis
wide
range
enantiopure
non-natural
α-substituted
tryptophans
high
yields
(up
to
99%
yield)
with
excellent
enantioselectivities
98%
ee).
Additionally,
synthetic
utility
this
protocol
demonstrated
through
scale-up
experiments
diverse
valuable
transformations.
Язык: Английский
One-Step Construction of Atropisomers Bearing 1,5-Central and Axial Chirality via Catalytic Diastereo- and Atroposelective Remote Desymmetrizing Alkynylation
ACS Catalysis,
Год журнала:
2024,
Номер
unknown, С. 18872 - 18883
Опубликована: Дек. 11, 2024
Catalytic
asymmetric
construction
of
atropisomers
with
multiple
stereogenic
elements
has
recently
become
an
emerging
area.
However,
general
methods
that
produced
bearing
remote
1,5-axial
and
central
chirality
efficiently
stereoselectively
are
scarce
yet
highly
challenging.
We
herein
report
a
catalytic
diastereo-
atroposelective
desymmetrizing
alkynylation
axially
prochiral
dialkynes
ortho-quinone
methides
(o-QMs),
furnishing
1,5-remote
centrally
elements.
The
control
axis
far
from
the
reaction
site
could
be
simultaneously
achieved
during
stereoselective
C(sp3)–C(sp)
bond-forming
process
to
generate
center.
In
addition,
kinetic
resolution
racemic
alkynes
via
o-QMs
been
developed,
further
enriching
structural
diversity
1,5-central
axial
chirality.
present
method
expands
chemical
space
atropisomeric
molecules
chiral
by
facile
downstream
diversification
C–C
triple
bonds.
Finally,
can
also
applied
for
motifs
1,9-
1,10-stereogenic
centers.
Язык: Английский
Enantioselective Vinylogous Addition of Enones to Allenes Enabled by Synergistic Borane/Palladium Catalysis
Journal of the American Chemical Society,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 24, 2024
Herein,
we
report
a
method
for
enantioselective
vinylogous
addition
of
enones
to
alkoxyallenes
enabled
by
synergistic
borane/palladium
catalysis.
The
inductive
effect
provided
borane
coordination
the
ketone
was
essential
closing
gap
between
conditions
needed
generation
dienolate
and
those
initiation
palladium
catalytic
cycle
protonation
metal
catalyst.
Furthermore,
accomplished
first
example
stereodivergent
synthesis
with
chiral
borane/transition-metal
catalysts.
Язык: Английский