Organic Letters,
Год журнала:
2024,
Номер
26(42), С. 9079 - 9084
Опубликована: Окт. 15, 2024
We
report
a
novel
halogen-bond-assisted
NHC-catalyzed
(dynamic)
kinetic
resolution
strategy
for
the
synthesis
of
axially
chiral
heterobiaryls.
A
class
quinolines
are
prepared
efficiently
in
excellent
enantioselectivities
(≤98%
ee)
employing
3-5
mol
%
NHC
catalyst.
Mechanistic
studies
reveal
indispensability
5-bromo-2-iodobenzaldehyde
this
reaction,
which
pivotal
halogen
bonding
interaction
plays
crucial
role
process.
Chemical Science,
Год журнала:
2024,
Номер
15(12), С. 4564 - 4570
Опубликована: Янв. 1, 2024
We
present
NHC-catalyzed
atroposelective
esterification
of
prochiral
dialdehydes,
delivering
enantioenriched
axially
chiral
diaryl
ethers.
Matched
kinetic
resolutions
amplify
the
enantioselectivity
by
removing
minor
enantiomers
via
over-functionalization.
ACS Catalysis,
Год журнала:
2024,
Номер
14(9), С. 6926 - 6935
Опубликована: Апрель 18, 2024
The
synthesis
of
N–N
axial
compounds
containing
aromatic
acyl
amides
using
common
acylation
reagents
remains
challenging.
We
describe
a
highly
atropenantioselective
N-aminoindoles
axes.
A
chiral
cyclic
isothiourea
is
used
as
the
sole
organic
catalyst
in
transformation
N-acylation
reaction.
Aroyl
chlorides
have
been
to
construct
atropisomeric
through
N-acylation.
N-aminoindole
products,
which
bear
stereogenic
axes,
were
synthesized
with
high
yields
and
enantioselectivities.
Some
enantiopure
products
exhibited
promising
antibacterial
activities
against
plant
pathogens.
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.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 24, 2025
An
N-heterocyclic
carbene-catalyzed
atroposelective
[3
+
3]
annulation
of
alkynyl
acylazoliums
with
benzothiazole
derivatives
has
been
developed
for
the
divergent
synthesis
axially
chiral
triaryl
2-pyranones
and
fused
2-pyridones.
The
regioselectivity
this
protocol
depends
on
structure
benzothiazoles
three
different
nucleophilic
centers.
obtained
frameworks
represent
a
new
class
arylheterocycle
atropisomers,
which
may
be
potentially
useful
in
medicinal
chemistry.
Synthesis,
Год журнала:
2023,
Номер
56(12), С. 1862 - 1872
Опубликована: Дек. 14, 2023
Abstract
The
construction
of
axially
chiral
alkene
frameworks
is
currently
one
hottest
topics
in
the
field
organic
synthetic
chemistry.
Compared
to
traditional
molecules,
such
as
biaryls,
heterobiaryls,
and
anilides,
synthesis
alkenes
far
more
challenging,
especially
for
acyclic
tetrasubstituted
analogues.
In
this
review,
we
summarized
development
strategies
analogues,
including
asymmetric
difunctionalization,
C–H
functionalization,
cross-coupling,
(dynamic)
kinetic
resolution,
allylic
substitution-isomerization.
1
Introduction
2
Synthesis
Cyclic
Tetrasubstituted
Axially
Chiral
Alkenes
3
Acyclic
4
Summary
Outlook
In
the
past
few
decades,
N-heterocyclic
carbenes
(NHCs)
open
new
field
of
organocatalysis
in
synthetic
organic
chemistry.
This
review
highlights
dramatic
progress
NHC-catalyzed
C−O
bond
formation
based
on
activation
aldehyde
C(sp2)−H
bonds.
The
oxidative
and
redox
transformations
for
synthesis
various
molecules
with
structural
diversity
complexity
are
summarized.
Furthermore,
methods
strategies
NHC
catalysis
emerging
continuously;
thus,
cooperative
Brønsted
acid,
hydrogen-bonding
catalyst,
transition-metal
photocatalyst
is
also
described.
Catalysts,
Год журнала:
2024,
Номер
14(4), С. 219 - 219
Опубликована: Март 22, 2024
In
the
past
few
decades,
N-heterocyclic
carbenes
(NHCs)
have
opened
new
field
of
organocatalysis
in
synthetic
organic
chemistry.
This
review
highlights
dramatic
progress
NHC-catalyzed
C–O
bond
formation
based
on
activation
aldehyde
C(sp2)–H
bonds.
The
oxidative
and
redox
transformations
for
synthesis
various
molecules
with
structural
diversity
complexity
are
summarized.
Furthermore,
methods
strategies
NHC
catalysis
emerging
continuously;
thus,
cooperative
Brønsted
acid,
hydrogen-bonding
catalyst,
transition-metal
photocatalyst
also
described.
NHC-catalyzed
desymmetrization
amidation
of
biaryl
dialdehydes
has
been
developed
for
NH-free
axially
chiral
thiourea.
Sequential
kinetic
resolution
enhances
the
chirality
induction
strategy,
expanding
applicable
scope.
