Abstract
A
formal
[4+3]
cycloaddition
of
2‐alkylidenetrimethylene
carbonates
with
quinazoline‐derived
azomethine
imines
is
described.
Under
Pd
catalysis,
the
reaction
works
efficiently
under
room
temperature
to
afford
angular
quinazoline‐fused
seven‐membered
N,N,O
‐heterocycles.
variety
cyclic
and
were
well
tolerated
mild
conditions.
This
work
demonstrates
synthetic
utility
decarboxylative
cycloadditions
for
synthesis
polycyclic
aromatic
molecules.
Organic Letters,
Год журнала:
2023,
Номер
25(27), С. 5011 - 5016
Опубликована: Июнь 29, 2023
Ligand-directed
divergent
synthesis
(LDS)
is
an
important
synthetic
tool
for
the
preparation
of
structurally
diverse
organic
molecules
without
tedious
steps
to
modify
substrates.
Herein,
we
introduce
realization
3,4-,
1,2-,
and
1,4-cyclization
benzo[d]isothiazole-1,1-dioxide-fused
azadienes
(BDAs)
through
LDS,
leading
tetrahydro-2H-pyrans,
oxazinanes,
tetrahydro-2H-1,5-oxazocines,
respectively.
Using
phosphinooxazoline
(PHOX)
ligands,
have
developed
a
[4
+
2]
cycloaddition
between
BDAs
substituted
2-alkylidenetrimethylene
carbonates,
providing
access
multi-substituted
chiral
tetrahydro-2H-pyrans
in
good
yields
with
excellent
enantio-,
diastereo-,
regioselectivities.
We
report
the
first
example
of
dearomative
(3
+
2)
cycloadditions
3-nitro(aza)-indole,
-benzofuran,
and
-benzothiophene
derivatives
in
presence
allenyl
sulfones,
using
sulfinate
ammonium
ion
pairs
as
organocatalytic
promoters.
The
methodology
provides
a
new,
facile,
efficient
protocol
for
synthesis
functionalized
2,3-fused
cyclopentannulated
indolines
dihydrobenzofurans.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(7), С. 5019 - 5028
Опубликована: Март 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.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 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 & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(42), С. 8593 - 8602
Опубликована: Янв. 1, 2023
A
palladium-catalyzed
decarboxylative
α-allylation
of
thiazolidinones
and
azlactones
with
aza-π-allylpalladium
zwitterionic
intermediates,
in
situ
generated
from
sulfonamido-substituted
allylic
carbonates,
is
successfully
developed.
This
method
allows
the
formation
a
series
structurally
diverse
5-alkylated
2-piperidones
under
mild
conditions
moderate
to
high
yields
(up
99%
yield).
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
88(1), С. 371 - 383
Опубликована: Дек. 23, 2022
A
cooperative
tertiary
amine/palladium-catalyzed
sequential
reaction
process,
proceeding
via
a
[4
+
3]
cyclization
of
isatin-derived
Morita-Baylis-Hillman
Expansion
(MBH)
carbonates
and
tert-butyl
2-(hydroxymethyl)allyl
followed
by
[1,3]-rearrangement,
has
been
found
developed.
range
structurally
diverse
spiro[methylene
cyclopentane-1,3′-oxindolines]
bearing
two
adjacent
β,γ-acyl
quaternary
carbon
stereocenters,
which
are
difficult
to
obtain
conventional
strategies,
were
obtained
in
good
yields.
Further
synthetic
utility
this
protocol
is
highlighted
its
excellent
regio-
stereocontrol
as
well
the
large-scale
synthesis
functional
transformations
compounds.
Moreover,
control
experiments
probably
established
plausible
mechanism
for
cyclization/[1,3]-rearrangement
process.
