The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(12), P. 8363 - 8375
Published: June 7, 2024
Palladium-catalyzed
decarboxylation
of
5-methylene-1,3-oxazinan-2-ones
and
5-methylene-1,3-dioxan-2-ones
to
generate
aza-π-allylpalladium
oxa-π-allylpalladium
1,4-dipoles
for
[4
+
2]
cycloaddition
reaction
with
1,3,5-triazinanes
was
developed,
affording
a
wide
range
hexahydropyrimidine
1,3-oxazinane
derivatives
in
good
excellent
yields
(up
99%).
The
acyclic
sulfonamido-substituted
allylic
carbonates
as
1,4-dipole
precursors
also
apply
the
developed
synthesized
strategy,
achieving
synthesis
hexahydropyrimidines.
Moreover,
situ-generated
undergoing
dimeric
4]
were
demonstrated
by
construction
1,5-diazocane
derivatives.
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(11), P. 3024 - 3029
Published: Jan. 1, 2023
Inspired
by
a
fungicide,
we
designed
5-vinyloxazolidine-2,4-diones
as
new
precursors
of
π-allylpalladium
zwitterionic
intermediates
and
developed
palladium-catalyzed
asymmetric
(5
+
3)
cycloaddition
with
azomethine
imines
(3
2)
1,1-dicyanoalkenes.
Both
reactions
proceeded
smoothly
under
mild
reaction
conditions
to
produce
various
chiral
heterocyclic
compounds
in
high
yields
excellent
enantioselectivities.
These
results
revealed
that
were
type
suitable
precursor
for
palladium
catalysis
will
find
extensive
applications
Pd-catalyzed
such
allylic
alkylation.
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.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(8), P. 1589 - 1594
Published: Feb. 22, 2024
This
study
demonstrates
a
highly
efficient
regiodivergent
ligand-controlled
palladium-catalyzed
cycloaddition
reaction
of
vinyloxazolidine-2,4-diones
with
1,3,5-triazinanes.
In
the
presence
diphosphine
ligand,
proceeds
via
(5+2)
pathway
to
afford
1,3-diazepin-4-ones
in
excellent
yields,
while
using
monophosphine
smoothly
(3+2)
give
imidazolidin-4-ones
good
yields.
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).
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
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(7), P. 5019 - 5028
Published: March 19, 2024
In
this
paper,
we
reported
the
palladium-catalyzed
formal
[5
+
4]
cycloaddition
reactions
between
4-vinyl-4-butyrolactones
(VBLs)
and
azadienes.
Under
mild
reaction
conditions,
a
wide
range
of
benzofuran-fused
9-membered
heterocyclic
compounds
had
been
provided
in
moderate
to
excellent
yields
with
exclusive
regioselectivities
diastereoselectivities.
The
practical
applicability
synthesis
was
demonstrated
through
scale-up
further
transformation.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(34), P. 6328 - 6333
Published: Aug. 23, 2023
The
5-allenyloxazolidine-2,4-diones
had
been
synthesized
as
novel
precursors
of
π-allyl
palladium
zwitterion
and
were
applied
in
a
palladium-catalyzed
enantioselective
(3
+
2)
annulation
by
using
barbiturate-derived
alkenes
the
reaction
partner
presence
an
axially
chiral
phosphoramidite
ligand.
This
proceeded
smoothly
under
mild
conditions,
affording
highly
functionalized
spirobarbiturate-γ-lactam
derivatives
excellent
yields
along
with
high
diastereo-
enantioselectivities.
scale-up
further
transformation
product
also
successful.
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.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(23), P. 5971 - 5977
Published: Jan. 1, 2023
A
palladium-catalyzed
enantioselective
decarboxylative
allylic
alkylation
of
α-benzyl
cyanoacetates
with
methylene
cyclic
carbamates
was
developed
for
the
construction
nitrile-containing
acyclic
quaternary
carbon
stereocenters
good
results.
