Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(12), P. 2030 - 2035
Published: March 20, 2023
Ten-membered
lactones
are
the
core
units
of
many
biologically
active
natural
products
but
with
a
great
synthetic
challenge.
Based
on
principle
vinylogy,
novel
types
cyclic
vinylogous
anhydrides
have
been
designed
as
five-carbon
carbonyl
synthons,
further
applied
in
[5
+
5]
annulation
vinylethylene
carbonates
under
chiral
palladium
catalysis.
This
strategy
features
excellent
regioselectivity,
mild
conditions,
and
broad
substrate
scope,
affording
range
spiro
ten-membered
bearing
oxindole
pyrrolidinone
motif
yield
(up
to
99%)
moderate
high
enantioselectivity
89%
ee).
The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(9), P. 6025 - 6037
Published: April 18, 2022
A
dearomatization
process
of
3-nitroindoles
enabled
using
palladium-catalyzed
decarboxylative
[4
+
2]
cycloaddition
either
2-alkylidenetrimethylene
carbonates
or
2-(hydroxymethyl)-3-arylallyl
has
been
developed,
affording
a
wide
range
indoline-fused
tetrahydropyrans
in
good
yields
with
excellent
diastereoselectivities.
This
reaction
features
substrate
scope
and
mild
conditions
represents
the
first
example
application
π-allyl
palladium
1,4-[O,C]-dipole
species
for
dearomative
electron-deficient
heteroarenes.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(13), P. 1774 - 1777
Published: Jan. 1, 2024
A
novel
approach
for
the
synthesis
of
unsaturated
7-membered
lactones
by
Pd-catalyzed
[5+2]
dipolar
cycloaddition
vinylethylene
carbonates
(VECs)
and
C5-substituted
Meldrum's
acid
derivatives
has
been
developed.
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.
Chinese Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
42(10), P. 3051 - 3051
Published: Jan. 1, 2022
Chiral
heterocyclic
compounds
are
an
important
class
of
chiral
substances,
which
widespread
in
many
drugs,
pesticides
and
catalysts.Therefore,
the
efficient
asymmetric
synthesis
these
becomes
a
research
hotspot
organic
synthesis.Transition
metal-catalyzed
cyclization
with
heteroatom-dipole
precursors
is
method
to
construct
frameworks.Among
them,
designed
based
on
transition
allyl
or
propargyl
substitutions
have
been
extensively
studied
past
two
decades
occupied
role
this
field.The
cyclizations
introduced
detail.The
advantages
existing
problems
current
methods
analyzed,
would
provide
useful
reference
for
researchers
related
fields.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(11), P. 2648 - 2652
Published: Jan. 1, 2023
Herein,
we
disclose
the
first
Pd-catalyzed
enantioselective
(4
+
3)
cycloaddition
of
N
-2,2,2-trifluoroethylisatin
ketimines
with
2-methylidenetrimethylene
carbonate.
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.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(30), P. 5624 - 5629
Published: July 24, 2023
A
tandem
allylic
amination/oxa-Michael
addition
of
vinyl
methylene
cyclic
carbonates
(VMCCs)
has
been
developed
to
construct
heterocycles
by
single
palladium
catalysis
or
palladium-organo
relay
catalysis.
In
this
process,
the
bisnucleophiles
first
underwent
regioselective
amination,
and
then
second
nucleophilic
group
further
completed
hetero-Michael
reaction
form
a
series
heterocycles.
Among
them,
chiral
3,4-dihydro-2H-benzo[b][1,4]oxazines
could
be
produced
in
medium
high
yield
with
good
enantioselectivity
under
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(5), P. 3413 - 3418
Published: Feb. 20, 2024
An
efficient
cascade
intramolecular
cyclization/intermolecular
nucleophilic
addition
reaction
of
allenyl
benzoxazinone
with
isatin
or
isatin-derived
ketimine
has
been
established
by
using
Pd0-π-Lewis
base
catalysis.
A
series
3-hydroxy-2-oxindoles
and
3-amino-2-oxindoles
quaternary
carbon
atoms
at
the
C3
position
were
synthesized
in
good
yields
under
mild
conditions
through
this
protocol.
