Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
366(2), P. 269 - 276
Published: Nov. 30, 2023
Abstract
Here
we
present
a
[3+2]
cycloaddition
of
rationally
designed
trisubstituted
cyclic
α‐chloroamides,
primarily
those
incorporating
pharmacological
pyrazolone
cores,
as
potent
synthons
for
synthesizing
valuable
spirocyclic
γ‐lactam
architectures.
This
protocol
exhibits
52–96%
yields,
impressive
substrate
compatibility,
and
scale‐up
capacity.
Importantly,
this
study
also
represents
one
the
rare
examples
that
harness
enaminone
C−N
bond
cleavage
to
engineer
relevant
skeletons
biological
interest.
Moreover,
propose
plausible
mechanistic
explanation
elucidate
outstanding
chemical
outcomes
observed,
thereby
enriching
synthetic
toolbox
chemistry
α‐haloamide‐mediated
reactions.
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
60(43), P. 23187 - 23192
Published: Aug. 26, 2021
Abstract
An
unprecedented
enantioselective
synthesis
of
spiro‐γ‐lactams
via
a
sequential
C−H
olefination/asymmetric
[4+1]
spirocyclization
under
simple
Co
II
/chiral
spiro
phosphoric
acid
(SPA)
binary
system
is
reported.
A
range
biologically
important
are
obtained
with
high
levels
enantioselectivity
(up
to
98
%
ee
).
The
concise,
asymmetric
an
aldose
reductase
inhibitor
was
successfully
achieved.
Notably,
contrast
previous
reports
that
relied
on
the
use
cyclopentadienyl
or
its
derivatives
(achiral
Cp*,
Cp
tBu
,
chiral
x
)
ligated
III
complexes
requiring
tedious
steps
prepare,
cheap
and
commercially
available
cobalt(II)
acetate
tetrahydrate
used
as
efficient
precatalyst.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(39), P. 7214 - 7219
Published: Sept. 26, 2023
A
novel
Rh(III)-catalyzed
cascade
alkenyl
C-H
activation/[3
+
2]
annulation/pinacol
rearrangement
reaction
of
enaminones
with
iodonium
ylides
has
been
developed.
This
methodology
provides
a
new
and
straightforward
synthetic
strategy
to
afford
highly
functionalized
2-spirocyclo-pyrrol-3-ones
in
satisfactory
yield
from
readily
available
starting
materials
under
mild
conditions.
Moreover,
gram-scale
reactions
further
derivatization
experiments
are
implemented
demonstrate
the
potential
utility
this
developed
approach.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 28, 2025
We
report
herein
that
photoinduced
CO2•–
enabled
reductive
intramolecular
radical
cyclization
of
a
variety
aryl
iodide
derivatives
to
the
corresponding
phenanthridinone,
oxindole,
isoindolinone,
and
spirolactam
in
good
yields.
Preliminary
mechanistic
studies
suggested
generation
through
homolysis
cesium
formate
presence
light,
further
involvement
was
directly
proved
by
trapping
with
diphenyl
styrene
TEMPO.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(7), P. 1937 - 1942
Published: Jan. 1, 2022
An
iron-catalyzed
dearomative
spirocyclization
of
biaryl
ynones
with
sodium
metabisulfite
and
cycloketone
oxime
esters
is
developed
for
the
construction
sulfonated
spiro[5,5]trienones.
Helvetica Chimica Acta,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 30, 2025
Abstract
The
integration
of
sustainable
practices,
such
as
employing
renewable
light
sources
for
synthesizing
valuable
synthetic
scaffolds,
has
been
progressing
over
the
past
few
decades.
Among
these
noteworthy
organic
frameworks,
lactams,
particularly
γ‐lactams,
have
established
their
prominence
due
to
extensive
applications
in
pharmaceutical,
agricultural,
and
medicinal
domains.
This
growing
significance
γ‐lactams
spurred
considerable
interest
synthesis,
especially
via
milder,
more
sustainable,
environmentally
friendly
methods.
In
recent
years,
numerous
innovative
reaction
mechanisms
explored,
highlighting
how
photocatalysis
can
enable
formation
from
readily
accessible
precursors
through
C−N
bond
cyclization
processes.
review
emphasizes
potential
photocatalytic
strategies
not
only
enhance
current
methods
but
also
foster
development
greener
chemical
processes
future.
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(20), P. 7667 - 7678
Published: Jan. 1, 2024
Thiophene-fused
γ-lactams
are
reversible
covalent
inhibitors
of
the
SARS-CoV-2
main
protease,
a
nucleophilic
cysteine
enzyme.
γ-Lactams
can
inhibit
enzymes
by
S
-acylation
as
well
serine
O
-acylation.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 26, 2024
A
palladium-catalyzed
[2π
+
2σ]
cycloaddition
of
vinyl
bicyclo[1.1.0]butanes
with
methyleneindolinones
has
been
developed.
The
reaction
enables
the
construction
spirobicyclo[2.1.1]hexanes
bearing
an
all-carbon
quaternary
center
in
moderate
to
good
yields
excellent
diastereoselectivities.
This
method
features
a
broad
substrate
scope
functional
group
compatibility.
practical
utility
this
protocol
was
further
demonstrated
by
gram-scale
synthesis
and
postsynthetic
transformations
desired
product.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(2), P. 508 - 539
Published: Nov. 28, 2023
Molecules
with
spiro-linked
π-conjugated
structures
have
attracted
considerable
attention
in
the
realm
of
organic
functional
materials
due
to
their
advantageous
structural
features.
Angewandte Chemie,
Journal Year:
2021,
Volume and Issue:
133(43), P. 23371 - 23376
Published: Aug. 26, 2021
Abstract
An
unprecedented
enantioselective
synthesis
of
spiro‐γ‐lactams
via
a
sequential
C−H
olefination/asymmetric
[4+1]
spirocyclization
under
simple
Co
II
/chiral
spiro
phosphoric
acid
(SPA)
binary
system
is
reported.
A
range
biologically
important
are
obtained
with
high
levels
enantioselectivity
(up
to
98
%
ee
).
The
concise,
asymmetric
an
aldose
reductase
inhibitor
was
successfully
achieved.
Notably,
contrast
previous
reports
that
relied
on
the
use
cyclopentadienyl
or
its
derivatives
(achiral
Cp*,
Cp
tBu
,
chiral
x
)
ligated
III
complexes
requiring
tedious
steps
prepare,
cheap
and
commercially
available
cobalt(II)
acetate
tetrahydrate
used
as
efficient
precatalyst.
