Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(2), P. 443 - 448
Published: Jan. 10, 2023
A
modular
and
practical
click
chemistry
for
atroposelective
synthesis
of
1-triazolyl-2-naphthylamines
is
developed.
In
this
protocol,
a
variety
aromatic
or
aliphatic
azides,
1-alkynyl-2-naphthylamines
could
be
assembled
into
valuable
1-triazlyl-2-naphthylamine
scaffolds
via
[3
+
2]
cycloaddition
under
Rh-catalysis.
This
asymmetric
technology
features
easily
accessible
starting
materials,
mild
reaction
conditions,
facile
scalability,
good
enantioselectivity.
The
thermostability
products
showcases
great
applicable
potential,
the
synthetic
transformations
further
expand
molecular
diversity
atropisomers.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(14)
Published: Feb. 10, 2023
Axially
chiral
diaryl
ethers
are
a
type
of
unique
atropisomers
bearing
two
potential
axes,
which
have
applications
in
variety
research
fields.
However,
the
catalytic
enantioselective
synthesis
these
ether
is
largely
underexplored
when
compared
to
asymmetric
biaryl
or
other
types
atropisomers.
Herein,
we
report
highly
efficient
through
an
organocatalyzed
desymmetrization
protocol.
The
phosphoric
acid-catalyzed
electrophilic
aromatic
aminations
symmetrical
1,3-benzenediamine
substrates
afforded
series
excellent
yields
and
enantioselectivities.
facile
construction
heterocycles
by
utilizations
1,2-benzenediamine
moiety
products
provided
access
structurally
diverse
novel
azaarene-containing
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(17), P. 3477 - 3502
Published: Jan. 1, 2023
This
review
article
presents
an
in-depth
analysis
of
the
strategies
and
methodologies
for
using
chiral
phosphoric
acids
as
organocatalysts
in
asymmetric
syntheses
from
recent
literature.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(9), P. 1553 - 1557
Published: March 1, 2023
We
present
herein
a
highly
atroposelective
indolization
for
the
efficient
synthesis
of
1,1'-biheteroaryls
bearing
chiral
N-N
axis.
Under
cooperative
catalysis
phosphoric
acid
and
InBr3,
reactions
between
2,3-diketoesters
1,3-dione-derived
enamines
resulted
in
enantioselective
construction
1,1'-pyrrole-indoles
with
up
to
92%
yield,
94%
enantiomeric
excess
(ee),
or
bisindoles
ee.
Derivatizations
these
compounds
diverse
functionalized
linked
axially
biheteroaryls
have
also
been
demonstrated.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(3), P. 2127 - 2133
Published: Jan. 25, 2024
N-Heterocyclic
carbenes
(NHCs)
have
emerged
as
powerful
organocatalysts
in
controlling
the
stereoselectivities
of
reaction
sites
that
are
remote
from
catalyst-binding
position.
Meanwhile,
construction
a
stereogenic
center
at
δ-position
through
NHC
catalysis
remains
an
unmet
goal.
Herein,
we
report
NHC-catalyzed
enantioselective
1,6-conjugated
addition
formyl
enynes
with
nucleophiles
oxidative
LUMO
activation
strategy.
The
enables
efficient
chirality
control
enyne
substrates,
providing
access
to
high-value-added
enantio-enriched
pyrano[2,3-b]indole
and
pyrano[2,3-c]pyrazole
derivatives.
In
addition,
central-to-axial
transfer
oxidation
our
products
was
realized,
enabling
facile
axially
chiral
pyrans.
Journal of the American Chemical Society,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 5, 2025
We
herein
report
a
regioselective
synthesis
of
the
benzo[c]chromenol
core
via
cationic
rhodium-catalyzed
[2
+
2
2]
cycloaddition
1,7-enynes
with
tetrolic
acid
derivatives.
With
selection
an
appropriate
ligand,
both
regioisomers
could
be
obtained
in
excellent
regiomeric
ratio
and
enantiomeric
excess.
The
regioselectivity
was
governed
by
different
factors,
which
suggested
computational
studies.
Furthermore,
asymmetric
axially
chiral
cannabinol
bioisostere
candidate
achieved
transformation
from
central
chirality
to
axial
chirality.
Demonstration
natural
compound
also
depicted.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(51)
Published: Oct. 25, 2022
Axially
chiral
molecules
bearing
multiple
stereogenic
axes
are
of
great
importance
in
the
field
organic
chemistry.
However,
efficient
construction
atropisomers
featuring
two
different
types
has
rarely
been
explored.
Herein,
we
report
novel
atroposelective
synthesis
configurationally
stable
axially
B,N-heterocycles.
By
using
stepwise
asymmetric
allylic
substitution-isomerization
(AASI)
strategy,
diaxially
B,N-heterocycles
B-C
and
C-N
that
related
to
moieties
enamines
arylborons
were
also
obtained.
In
this
case,
all
four
stereoisomers
stereodivergently
afforded
high
enantioselectivities.
Density
functional
theory
(DFT)
studies
demonstrated
NH⋅⋅⋅π
interactions
played
a
unique
role
promotion
stereospecific
isomerization,
thereby
leading
highly
central-to-axial
chirality
transfer.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(27)
Published: March 6, 2023
Atropisomeric
heterobiaryls
play
a
vital
role
in
natural
products,
chiral
ligands,
organocatalysts,
and
other
research
fields,
which
have
aroused
great
interest
from
chemists
recent
years.
Until
now,
growing
number
of
optically
active
based
on
indole,
quinoline,
isoquinoline,
pyridine,
pyrrole,
azole,
benzofuran
skeletons
been
successfully
synthesized
through
metal
or
organic
catalytic
cross-coupling,
functionalization
prochiral
racemic
heterobiaryls,
ring
formation.
Among
different
strategies
for
the
atroposelective
synthesis
strategy
formation
has
become
tool
toward
this
goal.
In
review,
we
summarize
enantioselective
axially
approaches,
such
as
cycloaddition,
cyclization,
chirality
conversion.
Meanwhile,
reaction
mechanism
corresponding
applications
are
also
discussed.
