Advances in the Synthesis of Cyclopropylamines
Chemical Reviews,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 6, 2025
Cyclopropylamines
are
an
important
subclass
of
substituted
cyclopropanes
that
combine
the
unique
electronic
and
steric
properties
with
presence
a
donor
nitrogen
atom.
In
addition
to
their
in
diverse
array
biologically
active
compounds,
cyclopropylamines
utilized
as
synthetic
intermediates,
particularly
ring-opening
or
cycloaddition
reactions.
Consequently,
synthesis
these
compounds
has
constituted
significant
research
topic,
evidenced
by
abundant
published
methods.
widely
used
Curtius
rearrangement,
classical
cyclopropanation
methods
have
been
adapted
integrate
function
(Simmons-Smith
reaction,
metal-catalyzed
reaction
diazo
on
olefins,
Michael-initiated
ring-closure
reactions)
advances
enantioselective
synthesis.
More
recently,
specific
developed
for
preparation
aminocyclopropane
moiety
(Kulinkovich
reactions
applied
amides
nitriles,
cyclopropenes,
involving
C-H
functionalization,
...).
The
topic
this
review
is
present
different
cyclopropylamine
derivatives,
aim
covering
methodological
best
possible,
highlighting
scope,
stereochemical
aspects
future
trends.
Язык: Английский
Concise Synthesis of Optically Active Cyclopropane β-Amino Acid Derivatives via Olefination of Cyclopropanone Surrogates
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 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.
Язык: Английский
Formal Carbene Insertion into Cyclopropanones: Access to 2-Aroyl Cyclobutanones via Sulfonium Ylides
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 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.
Язык: Английский
Ring-Enlargement of in Situ Generated Cyclopropanones by the Reaction with Sulfonium Ylides: One-Pot Synthesis of Cyclobutanones
Organic Letters,
Год журнала:
2024,
Номер
26(46), С. 9871 - 9876
Опубликована: Ноя. 8, 2024
In
this
report,
we
describe
a
simple
method
for
the
synthesis
of
2-aryl-2-vinyl-cyclobutanones
through
reaction
in
situ
generated
cyclopropanones
and
cinnamylsulfonium
ylides,
representing
an
example
formal
carbene
insertion
into
these
three-membered
rings.
The
cyclobutanones
thus
obtained
are
ideal
substrates
palladium-catalyzed
coupling
reactions
upon
enol
triflate
formation,
thereby
providing
access
to
densely
functionalized
cyclobutenes.
A
mechanistic
proposal
ring-enlargement
is
presented
based
on
experimental
evidence.
Язык: Английский