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.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(9), P. 1332 - 1384
Published: March 14, 2023
Abstract
Conjugated
and
non‐conjugated
allenones
appear
as
recurring
motifs
in
organic
synthesis,
natural
products
mechanistic
investigations
showing
unique
properties
applications.
The
ability
of
to
build
cycles
has
provided
a
direct
access
strained
systems,
medium‐sized
rings,
arenes,
heterocycles
complex
polycycles.
In
addition,
have
served
models
catalysis.
critic
compilation
herein
presented
will
provide
an
exhaustive
overview
the
synthetic
possibilities
may
offer,
which
certainly
inspire
our
community
their
search
more
efficient
methodologies,
preparation
biological
pharmaceutical
targets,
improve
knowledge
theoretical
chemistry.
Great
part
this
review
discuss
aspects,
catalysis
innovation
insights
chemical
transformations
implying
allenone
motif.
many
examples
on
total
synthesis
pharmacologically
active
compounds
be
described.
We
hope
that
attractive
chemistry,
catalysis,
medicinal
chemistry
communities.
magnified
image
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(11), P. 3893 - 3900
Published: Jan. 1, 2024
An
organocatalyzed
asymmetric
synthesis
of
C
sp2
–N
atropisomers
by
formal
–O
amination
has
been
established
from
3-alkynyl-3-hydroxyisoindolinones
and
1-methylnaphthalen-2-ols.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(9), P. 2477 - 2484
Published: Jan. 1, 2024
A
variety
of
optically
active
tertiary
propargylic
alcohols
and
tetrasubstituted
2,3-allenoic
acids
have
been
synthesized
via
a
Pd((
R
)-DTBM-SEGphos)Cl
2
-catalyzed
carboxylative
kinetic
resolution
reaction
racemic
alcohols.
Molecules,
Journal Year:
2022,
Volume and Issue:
28(1), P. 12 - 12
Published: Dec. 20, 2022
BINOL
derivatives
have
shown
relevant
biological
activities
and
are
important
chiral
ligands
catalysts.
Due
to
these
properties,
their
asymmetric
synthesis
has
attracted
the
interest
of
scientific
community.
In
this
work,
we
present
an
overview
most
efficient
methods
obtain
BINOLs,
highlighting
use
metal
complexes
organocatalysts
as
well
kinetic
resolution.
Further
derivatizations
BINOLs
also
discussed.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(20), P. 4238 - 4243
Published: March 16, 2024
Abstract
The
catalytic
asymmetric
dearomative
arylation
of
2‐naphthols
enabled
by
the
unconventional
reactivity
o
‐quinone
diimides,
i.
e.
1,4‐conjugate
addition
on
quinone
sp
2
hybridized
carbon,
has
been
established.
Under
catalysis
chiral
phosphoric
acid,
various
cyclohexaenones
bearing
an
all‐carbon
quaternary
stereocenter
have
prepared
with
excellent
yields
and
enantioselectivities.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 30, 2025
A
regioselective
[3
+
2]
annulation
of
β,γ-alkynyl-α-ketimino
esters
with
1,3-dicarbonyls
is
disclosed.
series
Z-selective
dihydrofurans
bearing
an
exocyclic
double
bond
and
a
quaternary
carbon
center
are
accessed
without
the
usage
base.
Control
deuterium-labeling
experiments
have
been
investigated
to
probe
into
reaction
mechanism.
The
catalyst
base-free
nucleophilic
addition
highlights
transformation.
Beilstein Journal of Organic Chemistry,
Journal Year:
2021,
Volume and Issue:
17, P. 2729 - 2764
Published: Nov. 15, 2021
In
recent
years,
the
synthesis
of
axially
chiral
compounds
has
received
considerable
attention
due
to
their
extensive
application
as
biologically
active
in
medicinal
chemistry
and
ligands
asymmetric
catalysis.
Chiral
phosphoric
acids
are
recognized
efficient
organocatalysts
for
a
variety
enantioselective
transformations.
this
review,
we
summarize
development
acid-catalyzed
wide
range
biaryls,
heterobiaryls,
vinylarenes,
N-arylamines,
spiranes,
allenes
with
high
efficiency
excellent
stereoselectivity.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(3), P. 1815 - 1827
Published: Jan. 16, 2023
A
process
based
on
the
organocatalyzed
Mannich/cycloketalization/transesterification
tandem
reaction
of
1-(2-hydroxyaryl)-1,3-diketones
and
β,γ-alkynyl
α-imino
esters
has
been
developed,
delivering
a
variety
tricyclic
furanobenzodihydropyrans
with
excellent
results
(up
to
99%
yield,
ee,
>19:1
dr).
Advanced Synthesis & Catalysis,
Journal Year:
2021,
Volume and Issue:
364(2), P. 274 - 280
Published: Oct. 21, 2021
Abstract
An
enantioselective
synthesis
of
unnatural
pyrazole‐based
α‐chiral
amino
acid
derivatives
from
the
asymmetric
reaction
N
‐aryl‐5‐aminopyrazoles
with
β,γ‐alkynyl‐α‐imino
esters
using
a
chiral
spirocyclic
phosphoric
catalyst
was
developed.
Using
established
methodology,
various
α‐amino
tetrasubstituted
carbon
stereocenters
were
obtained
in
67–98%
yields
and
73–99%
enantioselectivities.
The
NH
2
functionality
corresponding
products
enables
further
transformations
to
thiourea
lactam.
magnified
image
