Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(49), P. 7483 - 7505
Published: Jan. 1, 2023
Copper-catalyzed
decarboxylative
reactions
are
powerful
strategies
for
the
construction
of
widely
available
skeletons
such
as
allenes,
ethynyl-containing
heterocycles,
and
quaternary
carbon
centers.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(5), P. 1314 - 1321
Published: Jan. 1, 2024
A
new
class
of
chiral
bipyridine-2NO
ligands,
which
incorporate
the
advantages
both
bipyridine
skeleton
and
pyrroloimidazolone-based
N
-oxide
moiety,
was
developed.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(13), P. 1474 - 1480
Published: March 1, 2024
Comprehensive
Summary
The
privileged
C
2
‐symmetric
rigid
phenol‐type
ligand
is
more
attractive
but
challenging
in
asymmetric
catalysis.
Herein,
we
designed
and
synthesized
a
class
of
rigid‐featured
chiral
tridentate
Phenol‐2NO
ligands,
that
incorporate
the
advantages
both
phenol
skeleton
pyrroloimidazolone‐based
N
‐oxide
moiety,
from
readily
available
L
‐prolinamides
operationally
simple
two
steps
up
to
44%
overall
yield.
More
importantly,
using
an
achiral
quinoline
derivative
as
additive,
newly
developed
could
serve
anioic
upon
deprotonative
activation
coordinate
Zn(II)
form
highly
enantioselective
catalyst
for
Michael‐type
Friedel‐Crafts
alkylation
reaction
indoles
with
2,3‐dioxopyrrolidines.
Excellent
yields
(up
90%)
high
enantioselectivities
99%
ee)
are
obtained
wide
range
substrates
under
mild
conditions.
Experiments
DFT
calculations
revealed
mechanism
origins
enantioselectivity.
This
also
represented
first
ligand/metal
complex
by
organic
base
additive
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3310 - 3315
Published: April 8, 2024
A
catalyst
system
consisting
of
a
chiral
phosphoramidite
ligand
and
Pd2(dba)3·CHCl3
causes
the
decarboxylation
5-vinyloxazolidine-2,4-diones
to
generate
amide-containing
aza-π-allylpalladium
1,3-dipole
intermediates,
which
are
capable
triggering
dearomatization
3-nitroindoles
for
diastereo-
enantioselective
[3+2]
cycloaddition,
leading
formation
series
highly
functionalized
pyrroloindolines
containing
three
contiguous
stereogenic
centers
with
excellent
results
(up
99%
yield,
88:12
dr,
96%
ee).
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(47)
Published: Oct. 19, 2023
Abstract
The
alkyne
group
is
the
key
component
of
many
bioactive
molecules
and
versatile
synthetic
building
block,
thus
introduction
which
into
target
has
attracted
considerable
interest
from
scientists.
Moreover,
tertiary
quaternary
stereocenters
are
common
motifs
in
natural
products
drugs,
however,
asymmetric
construction
such
one
challenging
tasks
due
to
steric
congestion
multiple
stereospecific
substituents
attached
carbon.
Metal–allenylidene
an
excellent
type
electrophilic
species.
addition
carbon‐nucleophiles
at
Cγ
metal–allenylidene
provides
effective
way
construct
as
well
introduce
group.
In
this
review,
state‐of‐the‐art
propargylic
C−C
bond
formation
via
metal‐allenylidene
generated
situ
alcohol
derivatives
presented.
Synthetic
applications,
mechanistic
insights
addressed.
challenges
opportunities
field
also
discussed.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 10, 2025
A
palladium-catalyzed
decarboxylative
allylic
sulfonylation
reaction
of
vinyloxazolidine-2,4-diones
with
inexpensive
and
readily
available
sodium
sulfinates
as
reagents
has
been
developed.
Under
the
catalysis
Pd(PPh3)4,
a
wide
range
γ-sulfonyl-α,β-unsaturated
amides
can
be
synthesized
in
good
to
excellent
yields.
The
developed
protocol
is
characterized
by
exclusive
regioselectivity,
mild
conditions,
broad
substrate
scope,
functional
group
tolerance,
suitable
for
gram-scale
synthesis.
