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).
Chemical Society Reviews,
Год журнала:
2022,
Номер
51(10), С. 4146 - 4174
Опубликована: Янв. 1, 2022
The
advances
on
metal-catalysed
high-order
dipolar
annulations
were
comprehensively
summarized
in
this
review.
To
further
exploit
the
potential
of
unique
annulation
strategy,
a
research
outlook
was
also
proposed.
Chemical Society Reviews,
Год журнала:
2023,
Номер
53(2), С. 883 - 971
Опубликована: Дек. 18, 2023
This
review
aims
to
collect
advancements
in
enantioselective
palladium-catalyzed
cyclization
reactions
over
the
past
eleven
years,
and
it
is
organized
into
thirteen
sections
depending
on
different
types
of
transformations
involved.
Chemical Science,
Год журнала:
2023,
Номер
14(11), С. 3024 - 3029
Опубликована: Янв. 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,
Год журнала:
2024,
Номер
26(35), С. 7425 - 7430
Опубликована: Авг. 22, 2024
Presented
herein
is
an
atom-
and
step-economical
method
enabling
the
precise
assembly
of
a
heptacyclic
scaffold
containing
both
azocine
indoline
units
through
cascade
reactions
indolin-1-yl(aryl)methanimines
with
diazo
indanediones.
The
formation
products
involves
C–H
bond
activation
double
carbene
insertion
followed
by
intramolecular
condensation,
retro-[2
+
2]
cycloaddition,
recyclization.
This
reaction
not
only
provided
concise
straightforward
strategy
for
synthesis
otherwise
difficult
to
obtain
compounds
from
readily
available
substrates
but
also
disclosed
unprecedented
mode
derivatives
compounds.
In
general,
this
novel
synthetic
protocol
has
advantages,
such
as
easily
obtainable
substrates,
structurally
sophisticated
products,
procedure,
good
compatibility
diverse
functional
groups,
ready
scalability.
Moreover,
thus
obtained
showed
decent
antiproliferative
activity
against
three
human
cancer
cell
lines.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(24)
Опубликована: Апрель 8, 2024
We
here
reported
a
highly
stereoselective
method
for
the
synthesis
of
polysubstituted
conjugated
dienes
from
α-aryl
α-diazo
alkynyl
ketones
and
pyrazole-substituted
unsymmetric
aminals
under
mild
conditions,
which
was
promoted
by
photo-irridation
involved
with
1,6-dipolar
intermediate
quadruple
sigmatropic
rearrangements,
successfully
developed.
In
this
transformation,
cleavage
four
bonds
recombination
five
were
implemented
in
one
operational
step.
This
protocol
provided
modular
tool
constructing
amines,
pyrazoles
α-alkynyl-α-diazoketones
one-pot
manner.
The
results
mechanistic
investigation
indicated
that
plausible
reaction
path
underwent
1,6-sigmatropic
rearrangement
instead
1,5-sigmatropic
rearrangement.
Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(12), С. 3127 - 3165
Опубликована: Окт. 11, 2021
Abstract
Isoxazoles
are
an
important
class
of
heterocycles
with
nitrogen
and
oxygen
in
a
1,2‐relationship.
They
find
wide
applications
synthetic
organic
chemistry
part
several
drug
molecules.
Since
the
last
two
decades,
great
progress
has
been
achieved
synthesis
functionalization
isoxazoles,
which
transition
metal
catalysis
played
pivotal
role
towards
achieving
this
goal.
In
particular,
(TM)‐mediated
site‐selective
functionalizations
isoxazoles
retain
pharmacologically
synthetically
valuable
isoxazole
skeleton,
highly
appealing.
This
comprehensive
review
is
solely
dedicated
to
TM‐mediated
wherein
we
have
included
as
directing
groups
(DG)
for
TM‐catalyzed
C−H
reactions,
direct
functionalization,
along
cross‐coupling
reactions
annulation
finally
ring‐opening
under
TM‐catalysis
also
discussed.
Also,
incorporated
discussions
on
reaction
designs,
their
advantages
limitations,
mechanistic
details
challenges
that
need
be
addressed
inspire
medicinal
chemists
explore
new
arenas
make
use
key
scaffold.
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
41(21), С. 2825 - 2831
Опубликована: Июнь 25, 2023
Comprehensive
Summary
We
developed
a
novel
Pd‐catalyzed
[4
+
4]
cycloaddition
of
(benzo)furan‐derived
azadienes
with
homo‐TMM
all‐carbon
1,4‐dipoles
in
situ
generated
from
α
‐allyl
malonate
derivatives,
affording
an
array
benzofuro[3,2‐
b
]azocines
and
furo[3,2‐
good
to
excellent
yields
(up
96%)
exclusive
regioselectivities.
This
methodology
featured
mild
reaction
conditions
functional
group
tolerance.
The
synthetic
utility
was
demonstrated
by
gram‐scale
reaction.
Furthermore,
the
catalytic
asymmetric
version
has
also
been
explored.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
63(6)
Опубликована: Дек. 15, 2023
Abstract
We
report
herein
an
unprecedented
enantioselective
(4+4)
cycloaddition
of
simple
1,3‐dienes
with
azadienes
for
the
construction
fused
eight‐membered
N
‐heterocycles.
In
this
transformation,
π‐Lewis
basic
Pd(0)
catalyst
achieves
activation
to
induce
nucleophilic
addition
followed
by
ring
cyclization
via
a
selective
terminal
allylic
substitution.
Furthermore,
highly
efficient
and
diastereoselective
derivatizations
rings
provide
facile
access
diverse
enantiopure
tetra‐
hexacyclic
compounds
potential
application
in
medicinal
chemistry.
