European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(25)
Published: April 9, 2024
Abstract
A
formal
[4+2]
cycloaddition
reaction
of
ethynylethylene
carbonates
and
2‐aminophenols
has
been
developed
for
the
synthesis
3,4‐dihydro‐2
H
‐benzo[
b
][1,4]oxazines
bearing
quaternary
carbon
atoms.
The
features
mild
conditions,
good
functional
group
compatibility
yields.
Furthermore,
when
using
chiral
PyBox
ligand,
this
strategy
could
also
achieve
asymmetric
][1,4]oxazines.
Application
studies
indicated
that
hydroxymethyl
final
products
was
an
excellent
can
be
further
modified
easily.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(4), P. 2746 - 2757
Published: Feb. 7, 2024
Remote
stereocontrol
in
transition-metal
catalysis
is
a
challenging
but
interesting
research
topic.
In
this
work,
we
achieved
copper-catalyzed
asymmetric
yne-allylic
substitution
using
electron-rich
arenes
and
acyclic
carbonates
through
remote
enantioselectivity
control.
The
reaction
delivers
variety
of
enantioenriched
products
that
contain
diverse
set
valuable
moieties,
such
as
conjugated
enynes,
indoles,
indolizines,
allenes,
dihydrofurans,
which
are
widely
used
organic
synthesis
act
key
units
bioactive
molecules
natural
products.
synthetic
value
protocol
has
been
demonstrated
series
further
transformations,
mechanistic
studies
have
conducted
to
gain
more
insight
into
the
reaction.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(27), P. 5758 - 5763
Published: July 1, 2024
Anthrones
are
key
structural
motifs
in
many
natural
products
and
pharmaceutical
chemicals.
However,
due
to
its
unique
tricyclic
aromatic
structure,
the
synthetic
space
for
development
of
chiral
anthrone
derivatives
is
largely
limited.
By
utilizing
potential
copper-catalyzed
remote
asymmetric
yne-allylic
substitution
reaction,
we
describe
first
example
highly
regio-
enantioselective
on
various
esters
with
anthrones
under
a
mild
reaction
condition,
which
afforded
range
enantioenriched
1,3-enynes
exhibiting
broad
functional
group
tolerance
across
51
examples.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(30), P. 6407 - 6412
Published: July 19, 2024
Chiral
coumarins
and
their
derivatives
are
ubiquitous
structural
motifs
found
in
an
array
of
biologically
therapeutically
active
natural
products
drugs.
Herein,
a
highly
enantioselective
dual
remote
copper-catalyzed
vinylogous
alkynylallylic
substitution
yne-allylic
esters
with
has
been
developed.
The
practicality
this
method
is
exemplified
by
the
use
readily
available
starting
materials;
mild
reaction
conditions;
excellent
regio-,
enantio-,
stereoselectivities;
very
broad
substrate
scope
(67
examples),
while
scalability
further
applications
illustrated
gram-scale
series
derivations
products.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(14), P. 3946 - 3951
Published: Jan. 1, 2024
A
copper-catalyzed
yne-propargylic
substitution
using
amines
as
nucleophiles
has
been
achieved
for
the
first
time,
affording
a
variety
of
having
diyne
moieties,
which
are
important
pharmacophores
in
many
bioactive
molecules.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 19, 2025
A
novel
protocol
for
the
chemically
divergent
synthesis
of
chiral
oxacycles
has
been
developed
using
organo/metal
relay
catalysis.
The
methodology
integrates
a
stereospecific
Mannich
reaction
between
β,γ-alkynyl-α-imino
esters
and
1,3-diones
catalyzed
by
bifunctional
squaramide,
followed
Lewis
acid-catalyzed
regioselective
annulation
reactions.
By
switching
acid
employed,
we
achieved
pathway
to
construct
structurally
related
pyran
furan
derivatives
from
common
intermediate.
(3+3)
(3+2)
products
were
obtained
in
high
yields
excellent
stereoselectivities.
Comprehensive
mechanistic
studies
conducted
establish
mechanism.
An
enantioselective
Cu(
i
)-catalyzed
propargylic
[3
+
2]
cycloaddition
reaction
for
the
synthesis
of
optically
active
oxygen
heterocycles
bearing
CF
3
-substituted
quaternary
stereocenters
has
been
realized.
