Russian Chemical Reviews,
Год журнала:
2024,
Номер
93(3), С. RCR5111 - RCR5111
Опубликована: Март 1, 2024
The
strained
structure
of
cyclopropanes
serves
as
a
kind
trigger
for
variety
chemical
transformations.
Among
others,
processes
involving
conjugated
unsaturated
systems
are
particular
interest.
bonds
characterized
by
the
possibility
flexibly
varying
their
reactivity
up
to
full
involvement
in
This
review
is
first
consider
options
implementing
idea
combining
strain
energy
and
synthetic
capacity
within
single
concept.
A
detailed
analysis
activated
numerous
carbodiene
heterodiene
presented.<br>
bibliography
includes
289
references.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(12), С. 2784 - 2790
Опубликована: Апрель 23, 2024
Abstract
Ytterbium
triflate
catalysed
domino
reaction
of
(3‐formyl‐4‐indolyl)‐derived
donor‐acceptor
cyclopropane
with
primary
amines
provides
a
simple
approach
to
an
unprecedented
tetracyclic
skeleton
in
which
tropane
system
is
peri
‐annulated
indole
core.
This
process
involves
the
formation
imine
and
its
(3+2)‐cross‐cycloaddition
moiety,
yielding
tropane‐fused
core
under
mild
conditions.
These
products
are
significant
interest
for
pharmacology
as
potential
hybrid
molecules
dual
mode
action.
Organic Letters,
Год журнала:
2024,
Номер
26(25), С. 5341 - 5346
Опубликована: Июнь 14, 2024
An
unprecedented
VCP-CP
(vinylcyclopropane-cyclopentene)
rearrangement
approach
has
been
established
herein
by
virtue
of
the
pyridine-boronyl
radical
catalyzed
intramolecular
ring
expansions.
This
metal-free
pathway
harnesses
readily
available
catalysts
and
unactivated
vinylcyclopropane
starting
materials,
providing
an
array
cyclopentene
derivatives
chemoselectively
under
relatively
mild
conditions.
Mechanistic
studies
support
idea
that
boronyl
engages
in
generation
allylic/ketyl
species,
thus
inducing
opening
cyclopropanes
following
cyclization
processes.
Chemical Science,
Год журнала:
2023,
Номер
14(18), С. 4893 - 4900
Опубликована: Янв. 1, 2023
An
enantio-
and
diastereoselective
Pd-catalysed
(3
+
2)
cycloaddition
of
bis(trifluoroethyl)
2-vinyl-cyclopropane-1,1-dicarboxylate
(VCP)
with
cyclic
sulfamidate
imine-derived
1-azadienes
(SDAs)
has
been
developed.
These
reactions
provide
highly
functionalized
spiroheterocycles
having
three
contiguous
stereocentres,
including
a
tetrasubstituted
carbon
bearing
an
oxygen
functionality.
The
two
geminal
trifluoroethyl
ester
moieties
can
be
manipulated
in
facially
selective
manner
to
afford
more
diversely
decorated
spirocycles
four
stereocentres.
In
addition,
reduction
the
imine
moiety
also
fourth
stereocentre
exposes
important
1,2-amino
alcohol
Organic Letters,
Год журнала:
2024,
Номер
26(19), С. 4111 - 4116
Опубликована: Май 8, 2024
By
integration
of
oxocarbenium
activation
and
Lewis
acid
coordination
via
conformational
proximity-driven,
Pd(II)-
or
Cu(I)-catalyzed
intramolecular
ketone
haloacylation,
regio-
stereoselective
heterolytic
ring-opening
1,5-haloacylation
cyclopropyl
ketones,
including
those
with
weak
single
alkyl
donors,
has
been
developed
for
the
synthesis
valuable
α-quaternary
halo-γ-butenolides.
The
vicinal
carboxylic
acceptors
are
no
longer
just
spectator
activators.
Further,
this
reaction
delivers
a
constant
regioselectivity
regardless
electronic
nature
substituents,
even
malonate.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(20), С. 14587 - 14600
Опубликована: Окт. 11, 2023
A
Yb(OTf)3-catalyzed
formal
(4
+
3)
cycloaddition
reaction
of
donor-acceptor
cyclopropanes
with
3-benzylideneindoline-2-thiones
as
sulfur-containing
4π
components
has
been
successfully
achieved.
series
functionalized
5,10-dihydro-2H-thiepino[2,3-b]indole
derivatives
were
synthesized
good
yields
and
moderate
to
diastereoselectivity.
The
described
herein
represented
the
inaugural
3-benzylideneindoline-2-thiones.
Abstract
We
report
ring-opening
reactions
of
donor–acceptor
(D–A)
cyclopropanes
with
a
variety
five-
and
six-membered
enolizable
azaheterocyclic
thiones,
using
Sc(OTf)3
as
catalyst
in
dichloromethane.
The
majority
these
systems
reacted
through
nucleophilic
S-attack
at
the
donor
position
cyclopropane.
5-Mercapto-1,3,4-triazoles
were
shown
to
give
products
formal
N-attack,
bearing
two
external
C-S
bonds
could
react
equivalents
D–A
cyclopropane
generate
difunctionalized
azaheterocycles.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(22), С. 15937 - 15946
Опубликована: Окт. 27, 2023
Herein,
we
present
the
first
ever
use
of
3-isopropylidene
oxindoles
as
electrophiles
in
vinylogous
Michael
initiated
ring
closure
reaction
(MIRC).
Among
various
alkylidene
used
enantioselective
spirocyclization
reactions,
isopropylidene
are
least
explored
to
date.
The
competing
reactivity
(electrophilicity
vs
nucleophilicity)
presence
a
chiral
organocatalyst
is
controlled
by
logical
selection
more
reactive
nucleophile.
methodology
produces
library
densely
substituted
highly
enantioenriched
spirocyclopropyl
with
excellent
yield
and
stereoselectivities.
Moreover,
synthesis
HIV-1
NNRT
inhibitor
indicates
importance
our
synthesized
spiro-cyclopropyl
oxindole
core.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(7), С. 1002 - 1011
Опубликована: Март 2, 2023
Abstract
An
access
to
functionalised
eight‐membered
carbocyclic
ring
compounds
was
developed
by
simply
stirring
an
unusual
vinylogous
Donor‐Acceptor
Cyclopropane
(DAC)
in
boiling
o
‐xylene.
Both
experimental
and
computational
studies
were
performed
explain
the
diastereoselectivity/regioselectivity
transfer
observed
provide
overall
picture
of
mechanism.
magnified
image
