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.
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.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(31)
Опубликована: Май 27, 2022
Abstract
We
herein
demonstrated
an
efficient
method
for
the
atroposelective
construction
of
nine‐membered
carbonate‐bridged
biaryls
through
vinylidene
ortho
‐quinone
methide
(VQM)
intermediates.
Diverse
products
with
desirable
pharmacological
features
were
synthesized
in
satisfying
yields
and
good
to
excellent
enantioselectivities.
In
subsequent
bioassays,
several
agents
showed
considerable
antiproliferative
activity
via
mitochondrial‐related
apoptosis
mechanism.
Further
transformations
produced
more
structural
diversity
may
inspire
new
ideas
developing
functional
molecules.
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.
Journal of Heterocyclic Chemistry,
Год журнала:
2024,
Номер
61(3), С. 528 - 537
Опубликована: Янв. 16, 2024
Abstract
A
dearomative
[4
+
2]
cycloaddition
of
3‐nitroindoles
ortho
‐amino
Morita−Baylis−Hillman
carbonates
was
established
under
mild
conditions.
This
method
provides
an
efficient
and
practical
approach
for
delivering
tetrahydro‐5
H
‐indolo[2,3‐
b
]quinolines
containing
three
contiguous
stereocenters,
two
tertiary
one
quaternary,
in
high
yield
(up
to
95%)
with
excellent
diastereoselectivity
(all
cases
>25:1
dr
).
The
potential
synthetic
applications
this
strategy
were
also
highlighted
by
the
scale‐up
experiment
further
transformation.
Moreover,
structure
relative
configuration
cycloadduct
unequivocally
confirmed
single‐crystal
X‐ray
diffraction.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(9), С. 6025 - 6037
Опубликована: Апрель 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.
ACS Catalysis,
Год журнала:
2023,
Номер
13(16), С. 10694 - 10704
Опубликована: Авг. 1, 2023
Developing
diversity-oriented
synthetic
approaches
for
medium-sized
rings
is
of
great
interest,
and
the
divergent
synthesis
with
different
ring
sizes
poses
a
challenging
task.
In
this
study,
we
present
catalyst-controlled
switchable
(5
+
4)/(3
4)
cycloaddition
strategy
seven-
nine-membered
heterocycles.
Utilizing
two
4-aminopyridine
Lewis
base
catalysts,
pyrazole-fused
benzazepines
or
benzoxazonines
can
be
efficiently
assembled
from
same
substrates.
These
products
exhibit
good
stability
without
interconversion
under
reaction
conditions
elevated
temperatures.
The
origin
chemoselectivity
was
elucidated
by
means
computational
studies
involving
DFT
calculations,
distortion/interaction
analysis,
noncovalent
interaction
analysis.
