Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(10), С. 2780 - 2785
Опубликована: Янв. 1, 2024
An
unprecedented
multi-component
reaction
with
solvent
participation
and
a
novel
conversion
of
sulfur
ylides
was
developed
via
Ugi/olefination
to
construct
pyrrolidin-5-one-2-carboxamides.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(6), С. 1521 - 1526
Опубликована: Янв. 1, 2023
A
highly
efficient
[4
+
1]
annulation
of
sulfur
ylide
salts
and
o
-sulfonamido
aldimines
for
construction
valuable
2,3-disubstituted
indolines
is
reported.
It
worth
noting
that
indoles
could
also
be
synthesized
by
this
cascade
reaction.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(42)
Опубликована: Сен. 2, 2022
Abstract
Spiro[azetidine‐indolines]
are
important
scaffolds
in
diverse
bioactive
compounds.
Current
efforts
to
synthesize
spiro[azetidine‐indolines]
limited
chiral
spiro[azetidine‐2,3′‐indolines].
Asymmetric
synthesis
of
structurally
similar
spiro[azetidine‐3,3′‐indolines]
remains
unexplored.
In
this
work,
the
first
copper(I)‐catalyzed
asymmetric
Kinugasa/aryl
C−C
coupling
cascade
reaction
is
described.
This
provides
a
straightforward
access
densely
functionalized
spiro[azetidine‐3,3′‐indoline]‐2,2′‐diones
good
yields
and
with
high
enantioselectivity.
Organic Letters,
Год журнала:
2022,
Номер
24(7), С. 1513 - 1517
Опубликована: Фев. 11, 2022
The
enantioselective
[3
+
1]-cycloaddition
of
racemic
donor-acceptor
(D-A)
aziridines
with
isocyanides
was
first
realized
under
mild
reaction
conditions
using
a
chiral
N,N'-dioxide/MgII
complex
as
catalyst,
providing
facile
route
to
enantioenriched
exo-imido
azetidines
good
excellent
yield
(up
99%)
and
enantioselectivity
94%
ee).
An
obvious
amplification
effect
observed
in
this
system,
an
explanation
elucidated
based
on
the
experimental
investigation
X-ray
crystal
structure
enantiomerically
pure
catalyst.
Abstract
This
review
introduces
the
synthetic
organic
chemical
value
of
α‐bromocarbonyl
compounds
with
tertiary
carbons.
compound
a
carbon
has
been
used
primarily
only
as
radical
initiator
in
atom
transfer
polymerization
(ATRP)
reactions.
However,
recent
development
photo‐radical
reactions
(around
2010),
research
on
use
alkyl
precursors
became
popular
2012).
As
more
examples
were
reported,
studied
not
radicals
but
also
for
their
applications
organometallic
and
ionic
That
is,
act
nucleophiles
well
electrophiles.
The
carbonyl
group
is
attractive
because
it
allows
skeleton
to
be
converted
after
reaction,
being
applied
total
synthesis.
In
our
survey
until
2022,
can
perform
full
range
necessary
synthesis,
including
multi‐component
reactions,
cross‐coupling,
substitution,
cyclization,
rearrangement,
stereospecific
asymmetric
α‐Bromocarbonyl
have
created
new
trend
alkylation,
which
then
had
limited
reaction
patterns
focuses
how
chemistry.
Organic Letters,
Год журнала:
2022,
Номер
24(15), С. 2837 - 2841
Опубликована: Апрель 8, 2022
A
concise
and
practical
strategy
via
potassium-carbonate-mediated
[3
+
2]-cycloaddition
reaction
of
α-halohydroxamates
with
the
common
solvent
carbon
disulfide
for
synthesis
functionalized
rhodanine
derivatives
in
good
to
excellent
yields
is
developed.
The
present
methodology
features
a
wide
substrate
scope
as
well
functional
group
tolerance.
potential
synthetic
utility
this
protocol
demonstrated
by
series
natural
product
containing
rhodamine
skeletons.
Encyclopedia of Reagents for Organic Synthesis,
Год журнала:
2025,
Номер
unknown, С. 1 - 5
Опубликована: Янв. 3, 2025
image
[5187‐82‐6]
C
6
H
13
BrO
2
S
(MW
229.14)
InChI
=
1S/C6H13O2S.BrH/c1‐4‐8‐6(7)5‐9(2)3;/h4‐5H2,1‐3H3;1H/q+1;/p‐1
InChIKey
JXFPTJYKYKVENJ‐UHFFFAOYSA‐M
(used
as
a
stabilized
precursor
of
sulfur
ylide
reagent
for
the
cycloaddition
reaction)
Physical
Data:
mp
86–88
°C.
1
Solubility:
soluble
in
O,
insoluble
some
organic
solvents,
such
hexane.
Form
Supplied
in:
white
crystalline
powder.
Analysis
Reagent
Purity:
spectroscopic
data:
IR
v
675,
694,
1133,
1364,
1395,
1525,
1621,
1656,
2923,
2976,
3326
cm
−1
and
NMR.
NMR
(400
MHz,
CDCl
3
)
δ
4.93
s
(2
,
SCH
),
4.12
q
CH
3.33
[6
(CH
S],
1.16
t
(3
(100
163.76
(CO),
63.43
(OCH
36.51
(SCH
25.20
[(CH
14.21
).
Preparative
Method:
solution
ethyl
bromoacetate
acetone
or
DMSO
was
stirred
under
nitrogen,
dimethyl
sulfide
added
one
portion
(eq
1).
A
precipitate
started
to
appear
immediately
became
thicker
upon
stirring.
After
stirring
6–18
h
at
room
temperature,
solid
filtered,
washed
with
acetone,
dried
vacuum
afford
sulfonium
salt
crystals.
Handling,
Storage,
Precautions:
(2‐ethoxy‐2‐oxoethyl)
bromide
is
stable
air.
The
can
be
stored
dry
well‐ventilated
place
should
protected
from
moisture.
Nature Communications,
Год журнала:
2025,
Номер
16(1)
Опубликована: Апрель 29, 2025
Since
its
advent
120
years
ago,
the
[2+n]
coupling
cyclization
of
ketene
has
been
prevalently
used
for
synthesis
N-
and
O-heterocycles.
In
contrast,
vinylogous
version,
i.e.,
use
alkenyl
as
4
C
synthon,
remain
elusive.
We
report
herein
that
in
rare
SN1-type
ring-opening
electron-deficient
cyclopropene,
initially
formed
sp2-carbocation-containing
zwitterionic
intermediate
undergoes
facile
1,4-alkoxy
migration
to
generate
a
functionalized
ketene.
This
electrophilic
not
only
allows
challenging
N-nucleophiles
be
engaged
conventional
reactions
(n
=
1
~
3),
also
unveiled
[4+n]
mode,
exemplified
by
[4
+
1]
formal
4]
construct
pyrrolidinone
azocine
frameworks.
The
protocol
offers
unified
entry
distinct
class
lactam
scaffolds
exhibit
anti-cancer
potential,
constituent
key
natural
product
scaffold
display
interesting
1e-
2e-
reactivities.
work
reveals
broader
synthetic
potential
SN1
type
cyclopropene
"dehydro"-donor-acceptor
cyclopropane
(DDAC)
substrate,
could
have
ramifications
chemistry,
N-heterocyclic
chemistry
related
medicinal
research,
well
donor-acceptor
system
chemistry.
Reactions,
Год журнала:
2024,
Номер
5(3), С. 492 - 566
Опубликована: Авг. 16, 2024
The
present
review
is
a
comprehensive
update
of
the
synthesis
monocyclic
β-lactams
via
cycloaddition
reactions.
According
to
IUPAC
definition
cycloaddition,
both
elementary
and
stepwise
processes
(formal
cycloadditions)
have
been
considered.
years
2019–2022
are
covered
by
cited
literature.
focus
on
synthetic
aspects
with
emphasis
structural
scope,
reaction
conditions,
mechanistic
aspects,
selectivity
results.
Selected
significant
data
related
biological
activities
applications
also
highlighted.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(47)
Опубликована: Окт. 10, 2022
Abstract
Aza‐oxyallyl
cations,
as
proposed
by
Sheehan
in
the
1960s
have
garnered
significant
attention
among
synthetic
organic
community,
owing
to
their
diverse
reactivity
profile
for
constructing
N‐scaffolds
of
biological
interest.
During
its
initial
growth,
aza‐oxyallyl
cations
were
used
effectively
a
3‐unit
synthon
1,3
dipoles
create
N‐heterocycles
via
cycloaddition
reactions,
wherein
cation
served
electrophilic
counterpart.
Recently,
new
variations
been
reported,
including
usage
1,4
dipole
domino
and
unique
alkylating
ability
heteroatoms.
This
review
article
provides
an
update
recent
developments
this
area
prevailing
mechanistic
insight.
Chemical Communications,
Год журнала:
2023,
Номер
59(53), С. 8270 - 8273
Опубликована: Янв. 1, 2023
Efficient
annulation
of
in
situ
formed
azaoxyallyl
cations
using
a
base
has
been
accomplished
with
diaziridines
to
provide
1,2,4-triazines
at
room
temperature.
The
substrate
scope,
scale
up,
functional
group
tolerance
and
transition-metal
free
reaction
conditions
are
the
important
practical
features.