ChemistrySelect,
Journal Year:
2024,
Volume and Issue:
10(1)
Published: Dec. 30, 2024
Abstract
The
development
of
novel
and
efficient
chiral
catalysts
has
always
been
a
focus
research
in
the
field
organic
synthesis.
In
this
paper,
we
present
design,
synthesis,
application
new
phase‐transfer
catalyst
derived
from
Dendrobine
alkaloid
using
simple
synthetic
methods
with
competitive
yields.
Meanwhile,
unique
skeleton
structure
our
was
conducive
to
induction
asymmetric
catalysis
successfully
utilized
alkylation
β
‐keto
esters,
leading
excellent
reactivity
good
enantioselectivity
formation
1H‐inden‐1‐ones.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(22)
Published: March 23, 2024
Abstract
Despite
the
significance
of
chiral
allene
skeletons
in
catalysis,
organic
synthesis
and
medicinal
chemistry
et
al.,
there
is
a
scarcity
reports
on
axially
allenyl
phosphorus
compounds.
Here,
we
disclosed
an
efficient
straightforward
cascade
reaction
between
ethynyl
ketones
phosphine
oxides,
resulting
broad
array
trisubstituted
allenes
incorporating
moiety
high
yields
with
excellent
stereoselectivities
facilitated
by
peptide‐mimic
phosphonium
salt
(PPS)
Additionally,
comprehensive
series
mechanistic
experiments
have
been
conducted
to
elucidate
that
this
proceeds
via
asymmetric
Pudovik
addition
followed
subsequent
phospha
‐Brook
rearrangement
occurs
concomitantly
kinetic
resolution,
representing
stereospecific
protonation
process
facilitating
central‐to‐axial
chirality
transfer
manner.
We
anticipate
our
research
will
pave
way
for
promising
exploration
novel
stereo‐induction
pattern
addition/
reaction.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(46)
Published: Aug. 1, 2024
Abstract
The
stereochemistry
of
shape‐persistent
molecular
cages,
particularly
those
resembling
prisms,
exerts
significant
influence
on
their
application‐specific
functionalities.
Although
methods
exist
for
fabricating
inherently
chiral
prism‐like
strategies
catalytic
asymmetric
synthesis
these
structures
in
a
diversity‐oriented
fashion
remain
unexplored.
Herein,
we
introduce
an
unprecedented
organocatalytic
desymmetrization
approach
the
generation
cages
via
phosphonium‐containing
foldamer‐catalyzed
S
N
Ar
reactions.
This
methodology
establishes
topological
connection,
enabling
facile
assembly
wide
range
versatile
stereogenic‐at‐cage
building
blocks
possessing
two
highly
modifiable
groups.
Furthermore,
subsequent
stereospecific
transformations
remaining
chlorides
and/or
ethers
afford
convenient
access
to
numerous
functionally
relevant
chiral‐at‐cage
molecules.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: May 22, 2024
Abstract
The
enantioselective
synthesis
of
S
-stereogenic
sulfinamides
has
garnered
considerable
attention
due
to
their
structural
and
physicochemical
properties.
However,
catalytic
asymmetric
still
remains
daunting
challenges,
impeding
broad
application
in
drug
discovery
development.
Here,
we
present
an
approach
for
the
through
peptide-mimic
phosphonium
salt-catalyzed
skeletal
reorganization
simple
prochiral
and/or
racemic
sulfoximines.
This
methodology
allows
facile
access
a
diverse
array
substituted
with
excellent
enantioselectivities,
accommodating
various
substituent
patterns
desymmetrization
or
parallel
kinetic
resolution
process.
Mechanistic
experiments,
coupled
density
functional
theory
calculations,
clarify
stepwise
pathway
involving
ring-opening
ring-closing
processes,
step
identified
as
crucial
achieving
stereoselective
control.
Given
prevalence
centers
pharmaceuticals,
anticipate
that
this
protocol
will
enhance
efficient
precise
relevant
chiral
molecules
analogs,
thereby
contributing
advancements
discovery.
Chinese Journal of Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 24, 2025
Comprehensive
Summary
In
this
study,
we
successfully
developed
ion
pair
catalysts
consisting
of
chiral
bisguanidinium
(BG)
cations
and
non‐chiral
sulphonated
phosphine‐palladium
complexes
as
counterions.
These
pairs
catalyzed
allylic
alkylation
reactions
with
excellent
enantioselectivities.
Furthermore,
these
can
be
easily
performed
on
a
gram‐scale,
demonstrating
their
potential
for
industrial
applications.
We
were
able
to
obtain
1
H
NMR
the
catalyst
identified
31
P
complex.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(42), P. 7705 - 7710
Published: Oct. 13, 2023
Chiral
P,N-ligands
are
of
great
interest
and
importance
in
the
fields
metal-catalyzed
enantioselective
transformations
have
found
numerous
applications
spanning
drug
polymer
synthesis.
Here,
modular
assembly
diverse
P-stereogenic
axially
chiral
phosphinooxazoles
ligands
is
achieved
through
palladium-catalyzed
asymmetric
cleavage
C-P
bond/intermolecular
C-H
bond
functionalization
high
atroposelectivities
diastereoselectivities
up
to
>99%
ee
>25:1
dr.
This
protocol
features
broad
substrate
scope
provides
an
avenue
for
facile
construction
new
directly
from
phosphonium
salts
benzoxazoles/benzothiazoles.
Evaluation
synthesized
two
model
catalytic
reactions
illustrates
potential
our
strategy
access
valuable
molecules.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
27(4), P. 1012 - 1017
Published: Jan. 21, 2025
Vicinal
bis(tetraarylphosphonium)
salts
have
scarcely
been
reported
in
the
literature.
In
this
study,
we
demonstrate
that
visible-light-induced
difunctionalization
of
ortho-trifluoromethylsulfonylated
diaryliodonium
conveniently
furnishes
bis(phosphonium)
without
additional
catalysts
or
photoinitiators.
The
methodology
establishes
a
practical
platform
for
preparation
using
readily
available
tertiary
phosphines.
are
anticipated
to
garner
great
deal
interest
catalytic
and
medicinal
chemistry.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(22)
Published: March 23, 2024
Abstract
Despite
the
significance
of
chiral
allene
skeletons
in
catalysis,
organic
synthesis
and
medicinal
chemistry
et
al.,
there
is
a
scarcity
reports
on
axially
allenyl
phosphorus
compounds.
Here,
we
disclosed
an
efficient
straightforward
cascade
reaction
between
ethynyl
ketones
phosphine
oxides,
resulting
broad
array
trisubstituted
allenes
incorporating
moiety
high
yields
with
excellent
stereoselectivities
facilitated
by
peptide‐mimic
phosphonium
salt
(PPS)
Additionally,
comprehensive
series
mechanistic
experiments
have
been
conducted
to
elucidate
that
this
proceeds
via
asymmetric
Pudovik
addition
followed
subsequent
phospha
‐Brook
rearrangement
occurs
concomitantly
kinetic
resolution,
representing
stereospecific
protonation
process
facilitating
central‐to‐axial
chirality
transfer
manner.
We
anticipate
our
research
will
pave
way
for
promising
exploration
novel
stereo‐induction
pattern
addition/
reaction.
