Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(41), P. 7562 - 7566
Published: Oct. 6, 2023
Stereoselective
synthesis
of
bicyclic
cyclopentanones
was
achieved
by
sequential
Tf2O-catalyzed
decarboxylation
and
intramolecular
[3
+
2]
cycloaddition
reactions
cyclic
enol
carbonates
bearing
an
alkene
unit.
Four
stereogenic
centers
in
the
obtained
cyclopentanone
were
stereoselectively
constructed.
This
method
could
be
applied
to
various
fused
products
moderate-to-good
yields.
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 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).
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(10), P. 2057 - 2061
Published: March 1, 2024
In
this
paper,
palladium-catalyzed
[3
+
2]
cycloaddition
of
4-vinyl-4-butyrolactones
with
ketenes
generated
from
easily
available
acyl
chlorides
was
achieved.
With
Pd2(dba)3·CHCl3/XantPhos
as
the
catalyst,
reaction
proceeded
smoothly
under
mild
conditions,
affording
a
series
2,3-dihydrofurans
in
moderate
to
high
yields.
The
scale-up
and
further
transformations
products
are
demonstrated,
plausible
mechanism
is
proposed
well.
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.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(5), P. 2722 - 2728
Published: Feb. 10, 2022
Palladium/boron-catalyzed
allylic
substitution
of
vinylethylene
carbonates
with
water
provides
a
powerful
approach
for
the
enantioselective
synthesis
tertiary
C–O
bond.
Density
functional
theory
calculations
in
present
work
show
that
nucleophilic
attack
via
distinctive
type
chelation-assisted
inner-sphere
pathway
is
responsible
experimentally
observed
regio-
and
enantioselectivities.
The
chelation
between
hydroxyl
group
boronate
moiety
Pd
center
enables
exclusive
branched-regioselectivity.
enantioselectivity
was
rationalized
terms
lone
pair---π
repulsive
interaction
O
atom
chelated
phenyl
ring
ligand.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(22), P. 3967 - 3972
Published: Oct. 18, 2022
Abstract
In
this
paper,
we
designed
and
synthesized
4‐vinyl‐4‐butyrolactone
as
a
precursor
to
generate
the
zwitterionic
allylpalladium
intermediates,
which
behaved
five‐membered
all‐carbon
synthon
in
palladium‐catalyzed
(5+3)
annulation
with
azomethine
imines,
giving
eight‐membered
ring‐fused
heterocycles
(26
examples,
49%
97%
yield,
>20:1
dr).
magnified
image
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.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
unknown, P. 5796 - 5805
Published: March 25, 2025
The
transition
metal-catalyzed
asymmetric
[n
+
2]
cycloaddition
reaction
with
oxy-substituted
ketene
intermediates
remains
a
synthetic
challenge
due
to
the
limited
availability
of
suitable
precursors.
Herein,
we
report
visible-light-driven,
palladium-catalyzed
[4
vinyl
benzoxazinanones
siloxyketene
intermediates,
generating
structurally
diverse
chiral
quinolinone
derivatives
satisfactory
diastereo-
and
enantioselectivities.
transient
generation
siloxyketenes
from
α-ketoacylsilylanes
through
visible-light-induced
Brook
rearrangement
is
important
for
success
present
cycloaddition.
13C-labeling
experiments
reveal
pathway
involving
[1,3]-silyl
migration
process.
side
arm
effects
BOX
ligand
silyl
steric
hindrance
α-ketoacylsilanes
play
crucial
roles
in
stereoselectivity
control,
theoretical
calculations
provide
insights
into
stereochemical
outcome
reaction.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(13), P. 2567 - 2572
Published: March 28, 2022
A
kinetically
controllable
strategy
toward
the
construction
of
otherwise
challenging
nine-membered
carbocycles
is
reported.
This
Pd-catalyzed
decarboxylative
procedure
utilizes
vinyl
methylene
cyclic
carbonates
as
C5-dipole
and
allylidenemalononitriles
C4-building
blocks.
The
protocol
features
user-friendly
operations
with
regioselectivity
generates
CO2
sole
byproduct.
formation
synthetically
valuable
thermodynamically
favored
seven-membered
was
also
investigated.
