Tetrahedron Chem,
Journal Year:
2024,
Volume and Issue:
9, P. 100070 - 100070
Published: Feb. 28, 2024
Bicyclo[1.1.0]butanes
(BCBs)
and
[1.1.1]propellanes
(tricyclo[1.1.1.01,3]pentanes,
TCPs)
are
structurally
unique
compounds
with
different
chemical
properties.
Strain-release
driven
reactions
have
emerged
as
an
atom-
step-economic
strategy
for
the
organic
synthesis.
Using
this
strategy,
a
variety
of
functional
ring
molecules
been
efficiently
synthesized,
including
various
cyclobutane
molecules,
bicyclo[2.1.1]hexanes,
bicyclo[1.1.1]pentanes,
others.
More
specifically,
these
strain
release-driven
include
aspects
nucleophilic
addition,
radical
electrophilic
or
transition
metal
catalysis.
This
review
will
discuss
recent
developments
in
strain-release
transformations
bicyclo[1.1.0]butanes
[1.1.1]propellanes.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(9)
Published: Jan. 22, 2024
The
spiro[3.3]heptane
core,
with
the
non-coplanar
exit
vectors,
was
shown
to
be
a
saturated
benzene
bioisostere.
This
scaffold
incorporated
into
anticancer
drug
sonidegib
(instead
of
meta-benzene),
vorinostat
phenyl
ring),
and
anesthetic
benzocaine
para-benzene).
patent-free
analogs
obtained
showed
high
potency
in
corresponding
biological
assays.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(48), P. 7467 - 7470
Published: Jan. 1, 2023
A
heteroannulations
of
bicyclobutane
derivatives
is
demonstrated
to
afford
spirocyclobutanes
with
cyclic
acetal
groups
via
the
Au-catalyzed
hydration
and
subsequent
intramolecular
cyclization.
Abstract
The
development
of
novel
strained
spiro
heterocycles
(SSHs)
as
bioisosteres
for
aromatic
or
non‐strained
aliphatic
rings
is
highly
sought
after
improving
drug
design.
Their
high
molecular
rigidity
and
predictable
vectorization
can
enhance
drug‐likeness,
target
selectivity
clinical
success.
Towards
this
goal,
1‐oxa‐2,6‐diazaspiro[3.3]heptane
(ODASE)
reported
a
potential
SSH‐bioisostere.
We
demonstrate
through
theoretical
studies
the
heterocycle
to
act
bioisostere
piperazine.
have
developed
its
synthesis
from
azabicyclo[1.1.0]butyl
intermediate
robust
mild
flow
technology‐assisted
two‐step
protocol.
Its
tolerance
stability
towards
medicinally
relevant
N
‐functionalisation
protocols
are
studied,
well
reduction
C3‐aminoalkylazetidinol
motif
found
in
anti‐cancer
cobimetinib.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 10, 2025
An
expedient
synthesis
of
cyclopropane
β-amino
acid
derivatives
is
reported
from
readily
accessible
cyclopropanone
surrogates.
The
addition
stabilized
phosphorus
ylides
to
1-sulfonylcyclopropanols
leads
the
formation
highly
electrophilic
alkylidenecyclopropanes
shown
be
reactive
in
a
telescopic
aza-Michael
reaction,
mild
conditions.
transformation
proceeds
with
complete
diastereocontrol
favor
trans
products
and
amenable
rapid
production
enantioenriched
derivatives,
peptidomimetics
spirocyclic
analogues.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 29, 2025
This
report
presents
a
method
for
the
synthesis
of
2-aroyl
cyclobutanones
via
reaction
in
situ-generated
cyclopropanones
with
acyl
sulfonium
ylides
representing
formal
carbene
insertion
into
cyclopropanones.
The
is
highly
stereoselective
case
2-substituted
cyclopropanones,
and
thus
obtained
are
well
suited
to
α-alkylation,
offering
versatile
synthetic
applications.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(28), P. 5389 - 5394
Published: July 6, 2023
An
expedient
approach
for
the
synthesis
of
challenging
β-fluoroamides
from
readily
accessible
cyclopropanone
equivalents
is
reported.
Following
addition
pyrazole
used
here
as
a
transient
leaving
group,
silver-catalyzed
regiospecific
ring-opening
fluorination
resulting
hemiaminal
leads
to
β-fluorinated