Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(42)
Published: July 23, 2024
Abstract
Catalytic
enantioselective
preparation
of
alkene
atropisomers
with
multiple
stereogenic
elements
and
discovery
their
applications
have
become
significant
but
challenging
issues
in
the
scientific
community
due
to
unique
structures
this
class
atropisomers.
We
herein
report
first
catalytic
atroposelective
cyclopentenyl[
b
]indoles,
a
new
kind
atropisomers,
point
axial
chirality
via
an
unusual
rearrangement
reaction
3‐indolylmethanols
under
asymmetric
organocatalysis.
Notably,
novel
type
promising
developing
chiral
ligands
or
organocatalysts,
discovering
antitumor
drug
candidates
fluorescence
imaging
materials.
Moreover,
theoretical
calculations
elucidated
possible
mechanism
non‐covalent
interactions
control
enantioselectivity.
This
approach
offers
synthetic
strategy
for
elements,
represents
3‐indolylmethanols,
which
will
advance
chemistry
indole
chemistry.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(3)
Published: Nov. 2, 2023
With
the
rapid
development
of
asymmetric
catalysis,
demand
for
enantioselective
synthesis
complex
and
diverse
molecules
with
different
chiral
elements
is
increasing.
Owing
to
unique
features
atropisomerism,
catalytic
atropisomers
has
attracted
a
considerable
interest
from
chemical
science
community.
In
particular,
introducing
additional
elements,
such
as
carbon
centered
chirality,
heteroatomic
planar
helical
into
provides
an
opportunity
incorporate
new
properties
axially
compounds,
thus
expanding
potential
applications
atropisomers.
Thus,
it
important
perform
transformations
synthesize
bearing
multiple
elements.
spite
challenges
in
transformations,
recent
years,
chemists
have
devised
powerful
strategies
under
organocatalysis
or
metal
synthesizing
wide
range
enantioenriched
Therefore,
become
emerging
field.
This
review
summarizes
progress
this
field
indicates
challenges,
thereby
promoting
horizon.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(8)
Published: Dec. 29, 2023
Abstract
In
the
chemistry
community,
catalytic
asymmetric
synthesis
of
furan‐based
compounds
bearing
both
axial
and
central
chirality
has
proven
to
be
a
significant
but
challenging
issue
owing
importance
difficulty
in
constructing
such
frameworks.
this
work,
we
have
realized
first
five‐five‐membered
via
organocatalytic
(2+4)
annulation
achiral
furan‐indoles
with
2,3‐indolyldimethanols
uncommon
regioselectivity.
By
strategy,
furan‐indole
were
synthesized
high
yields
excellent
regio‐,
diastereo‐,
enantioselectivities.
Moreover,
theoretical
calculations
conducted
provide
an
in‐depth
understanding
reaction
pathway,
activation
mode,
origin
selectivity.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 23, 2024
Abstract
Catalytic
enantioselective
preparation
of
alkene
atropisomers
with
multiple
stereogenic
elements
and
discovery
their
applications
have
become
significant
but
challenging
issues
in
the
scientific
community
due
to
unique
structures
this
class
atropisomers.
We
herein
report
first
catalytic
atroposelective
cyclopentenyl[
b
]indoles,
a
new
kind
atropisomers,
point
axial
chirality
via
an
unusual
rearrangement
reaction
3‐indolylmethanols
under
asymmetric
organocatalysis.
Notably,
novel
type
promising
developing
chiral
ligands
or
organocatalysts,
discovering
antitumor
drug
candidates
fluorescence
imaging
materials.
Moreover,
theoretical
calculations
elucidated
possible
mechanism
non‐covalent
interactions
control
enantioselectivity.
This
approach
offers
synthetic
strategy
for
elements,
represents
3‐indolylmethanols,
which
will
advance
chemistry
indole
chemistry.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 9, 2025
Transition-metal-catalyzed
[2
+
2
2]
annulation
of
alkynes
is
an
efficient
pathway
for
the
synthesis
aromatic
compounds.
However,
most
established
methods
require
noble
metal
catalysts.
Herein,
we
report
a
copper-catalyzed
intermolecular
diynes
with
through
vinyl
cation
intermediates,
enabling
atom-economical
preparation
biologically
important
carbazole
skeletons.
The
reaction
shows
good
regioselectivity
in
aryl(alkyl)alkynes.
Moreover,
preliminary
results
have
also
been
obtained
related
catalytic
atroposelective
transformation.
This
represents
rare
example
non-noble-metal-catalyzed
ynamides
pathway.
Nature Communications,
Journal Year:
2024,
Volume and Issue:
15(1)
Published: Aug. 10, 2024
The
construction
of
atropisomers
with
1,2-diaxes,
while
maintaining
high
enantiocontrol,
presents
a
significant
challenge
due
to
the
dynamic
nature
steric
hindrance
at
ortho-aryl
substituents.
Although
various
catalytic
asymmetric
methods
have
been
developed
for
accessing
axially
chiral
arylpyrroles,
synthesis
arylpyrroles
1,2-diaxes
in
manner
has
remained
rare.
Herein,
authors
report
diverse
and
C-C
C-N
axes
through
copper-catalysed
asymmetirc
[4
+
1]
annulation
yne-allylic
esters
arylamines
via
remote
stereocontrol
strategy.
This
approach
provides
facile
access
broad
range
heterobiaryl
(67
examples)
excellent
enantioselectivities,
each
bearing
one
or
two
C-C/C-N
axes,
demonstrating
its
versatility
efficiency.
utility
this
methodology
is
further
highlighted
by
transformation
product
into
phosphine
ligand,
thioureas
use
catalysis.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
27(10), P. 2509 - 2514
Published: March 5, 2025
Chiral
cyclobutanamide
is
a
privileged
scaffold
in
drug
discovery.
Here,
we
describe,
for
the
first
time,
synthesis
of
axially
chiral
cyclobutanamides
via
phosphoric
acid-catalyzed
enantioselective
condensation
between
N-arylcarbamyl
cyclobutanones
and
hydroxylamines.
Rational
substrate
design,
incorporating
an
amide
moiety
(CONHR)
into
cyclobutanone
backbone
formation
multi-hydrogen
bonding
network
involving
N-H
this
portion,
responsible
excellent
enantioselectivity
achieved
stereodetermining
dehydration
process,
which
supported
by
detailed
mechanistic
study.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 15, 2025
In
this
context,
we
report
a
nickel-catalyzed
dynamic
kinetic
asymmetric
reductive
arylation
of
aldehydes
with
racemic
heterobiaryl
triflates,
offering
series
axially
chiral
heterobiaryls
bearing
centrally
secondary
alcohol
moiety
in
highly
diastereo-
and
enantioselective
manner.
The
simultaneous
control
both
axial
central
stereogenic
elements
the
products
lies
stereoselective
nucleophilic
addition
configurationally
labile
hetereobiaryl
nickel
complex
to
formyl
group
aldehydes.
