Angewandte Chemie,
Год журнала:
2024,
Номер
136(30)
Опубликована: Май 15, 2024
Abstract
Atropisomers
hold
significant
fascination,
not
only
for
their
prevalence
in
natural
compounds
but
also
biological
importance
and
wide‐ranging
applications
as
chiral
materials,
ligands,
organocatalysts.
While
biaryl
heterobiaryl
atropisomers
are
commonly
studied,
the
enantioselective
synthesis
of
less
abundant
heteroatom‐linked
non‐biaryl
presents
a
formidable
challenge
modern
organic
synthesis.
Unlike
classical
atropisomers,
these
molecules
allow
rotation
around
two
bonds,
resulting
low
barriers
to
enantiomerization
through
concerted
bond
rotations.
In
recent
years
discovery
new
configurationally
stable
rare
scaffolds
such
aryl
amines,
ethers
sulfones
well
innovative
methodologies
control
configuration
have
been
disclosed
literature
constitute
topic
this
minireview.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(30)
Опубликована: Май 15, 2024
Atropisomers
hold
significant
fascination,
not
only
for
their
prevalence
in
natural
compounds
but
also
biological
importance
and
wide-ranging
applications
as
chiral
materials,
ligands,
organocatalysts.
While
biaryl
heterobiaryl
atropisomers
are
commonly
studied,
the
enantioselective
synthesis
of
less
abundant
heteroatom-linked
non-biaryl
presents
a
formidable
challenge
modern
organic
synthesis.
Unlike
classical
atropisomers,
these
molecules
allow
rotation
around
two
bonds,
resulting
low
barriers
to
enantiomerization
through
concerted
bond
rotations.
In
recent
years
discovery
new
configurationally
stable
rare
scaffolds
such
aryl
amines,
ethers
sulfones
well
innovative
methodologies
control
configuration
have
been
disclosed
literature
constitute
topic
this
minireview.
Beilstein Journal of Organic Chemistry,
Год журнала:
2025,
Номер
21, С. 55 - 121
Опубликована: Янв. 9, 2025
Axial
chirality
is
present
in
a
variety
of
naturally
occurring
compounds,
and
becoming
increasingly
relevant
also
medicine.
Many
axially
chiral
compounds
are
important
as
catalysts
asymmetric
catalysis
or
have
chiroptical
properties.
This
review
overviews
recent
progress
the
synthesis
via
organocatalysis.
Atroposelective
organocatalytic
reactions
discussed
according
to
dominant
catalyst
activation
mode.
For
covalent
organocatalysis,
typical
enamine
iminium
modes
presented,
followed
by
N
-heterocyclic
carbene-catalyzed
reactions.
The
bulk
devoted
non-covalent
activation,
where
Brønsted
acids
feature
most
prolific
catalytic
structure.
last
part
article
discusses
hydrogen-bond-donating
other
motifs
such
phase-transfer
catalysts.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(11), С. 7630 - 7643
Опубликована: Май 13, 2024
Atropoisomeric
chemotypes
of
diaryl
ethers-related
scaffolds
are
prevalent
in
naturally
active
compounds.
Nevertheless,
there
remains
considerable
research
to
be
carried
out
on
the
catalytic
asymmetric
synthesis
these
axially
chiral
molecules.
In
this
instance,
we
disclose
an
N-heterocyclic
carbene
(NHC)-catalyzed
ethers
via
atroposelective
esterification
dialdehyde-containing
ethers.
NHC
desymmetrization
produces
ether
atropisomers
with
high
yields
and
enantioselectivities
moderate
circumstances.
Chiral
compounds
may
precursors
for
highly
functionalized
bioactivity
ligands
catalysis.
Chemical Society Reviews,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 18, 2024
This
tutorial
review
provides
an
overview
of
various
important
structural
features
and
reactivity
modes
NHCs
delves
deep
into
the
recent
advances
in
NHC-organocatalysis.
Chemical Science,
Год журнала:
2024,
Номер
15(16), С. 5993 - 6001
Опубликована: Янв. 1, 2024
Axially
chiral
molecular
scaffolds
are
widely
present
in
therapeutic
agents,
natural
products,
catalysts,
and
advanced
materials.
The
construction
of
such
molecules
has
garnered
significant
attention
from
academia
industry.
catalytic
asymmetric
synthesis
axially
biaryls,
along
with
other
non-biaryl
molecules,
been
extensively
explored
the
past
decade.
However,
atroposelective
C-O
axial
chirality
remains
largely
underdeveloped.
Herein,
we
document
a
copper-catalyzed
compounds
using
novel
1,8-naphthyridine-based
ligands.
Mechanistic
investigations
have
provided
good
evidence
support
mechanism
involving
synergistic
interplay
between
desymmetrization
reaction
kinetic
resolution
process.
method
described
this
study
holds
great
significance
for
compounds,
promising
applications
organic
chemistry.
utilization
ligands
copper
catalysis
is
anticipated
to
find
broad
copper(i)-catalyzed
azide-alkyne
cycloadditions
(CuAACs)
beyond.
ACS Catalysis,
Год журнала:
2024,
Номер
14(9), С. 6667 - 6673
Опубликована: Апрель 16, 2024
C–O
axially
chiral
diaryl
ethers
play
important
roles
in
natural
products
and
bioactive
molecules,
but
because
of
the
low
rotational
barrier
strict
steric
hindrance
requirements,
catalytic
asymmetric
construction
still
remains
a
challenge.
Herein,
we
devised
strategy
employing
achiral
azlactone
for
desymmetrization
prochiral
diamines
under
catalysis
phosphoric
acid.
The
targeted
were
obtained
very
good
yields
(up
to
98%)
high
enantioselectivities
>99.5:0.5
er).
synthetic
utility
was
demonstrated
through
large-scale
reaction
transformations
products.
Moreover,
DFT
calculations
conducted
probe
origins
enantioselectivity.
Chemical Communications,
Год журнала:
2024,
Номер
60(54), С. 6837 - 6846
Опубликована: Янв. 1, 2024
Axially
chiral
biaryl
ethers
and
related
compounds
hold
valuable
potential
in
natural
products,
medicinal
chemistry,
catalysis;
however,
their
asymmetric
syntheses
have
always
been
overlooked
compared
to
other
biaryl/hetero-biaryl
atropisomers.
Unlike
the
later
class
molecules
bearing
a
single
axis,
former
category
possesses
unique
type
of
atropisomerism
two
axes.
Due
great
importance
diverse
research
domains,
catalytic
atropselective
ether
synthesis
has
recently
witnessed
an
upsurge.
This
highlight
article
provides
elaborated
view
on
developments
synthetic
methods
that
explored
achieve
dual
axial
chirality
scaffolds.
