Synlett,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 24, 2024
Abstract
Studies
on
the
transformations
of
some
functionalized
cycloalkene
derivatives
through
their
ring
olefin-bond
aziridination/aziridine
opening
with
fluoride
are
presented.
The
selected
model
compounds
submitted
to
fluorinative
functionalization
were
an
amino
ester
and
diesters
a
cyclohexene
skeleton
as
well
cyclopentene-fused
β-lactam.
Functionalization
proceeded
across
substrate-directed
diastereoselective
aziridination,
followed
by
fluoride-mediated
aziridine
or
intramolecular
lactonization
giving
fluorinated
lactone
derivatives.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(12)
Published: Jan. 27, 2024
Abstract
Chiral
cyclopentadienyl‐rhodium(III)
Cp
x
Rh(III)
catalysis
has
been
demonstrated
to
be
competent
for
catalyzing
highly
enantioselective
aziridination
of
challenging
unactivated
terminal
alkenes
and
nitrene
sources.
The
chiral
system
exhibited
outstanding
catalytic
performance
wide
functional
group
tolerance,
yielding
synthetically
important
valuable
aziridines
with
good
excellent
yields
enantioselectivities
(up
99
%
yield,
93
ee).
This
protocol
presents
a
novel
effective
strategy
synthesizing
enantioenriched
from
simple
alkenes.
Various
transformations
were
performed
on
the
aziridine
products,
illustrating
versatility
synthetic
potential
this
constructing
functionalized
compounds.
Organic Process Research & Development,
Journal Year:
2023,
Volume and Issue:
28(5), P. 1567 - 1575
Published: Sept. 11, 2023
A
new
and
highly
efficient
continuous
flow
process
is
presented
for
the
synthesis
of
aziridines
via
thermal
Baldwin
rearrangement.
The
was
initially
explored
using
traditional
batch
techniques
but
suffered
from
moderate
yields,
long
reaction
times,
diastereoselectivities.
Here
we
demonstrate
that
can
be
greatly
improved
upon
its
transfer
to
flow,
which
afforded
aziridine
targets
in
high
short
consistently
diastereoselectivities,
with
high-throughput
rendering
multigram
quantities
product
periods
time.
In
addition,
processing
extended
substrate
scope
including
several
examples
had
failed
mode,
thus
demonstrating
value
this
overlooked
entry
into
valuable
species.
Synlett,
Journal Year:
2024,
Volume and Issue:
unknown
Published: June 24, 2024
Abstract
Studies
on
the
transformations
of
some
functionalized
cycloalkene
derivatives
through
their
ring
olefin-bond
aziridination/aziridine
opening
with
fluoride
are
presented.
The
selected
model
compounds
submitted
to
fluorinative
functionalization
were
an
amino
ester
and
diesters
a
cyclohexene
skeleton
as
well
cyclopentene-fused
β-lactam.
Functionalization
proceeded
across
substrate-directed
diastereoselective
aziridination,
followed
by
fluoride-mediated
aziridine
or
intramolecular
lactonization
giving
fluorinated
lactone
derivatives.
