Recent Advances in Single-Electron Reduction-Induced Ring Opening of N-Acyl Cyclic Amines
Synthesis,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 16, 2025
Abstract
Cyclic
amines
represent
ubiquitous
structural
motifs
in
organic
chemistry,
prominently
featured
natural
products
and
pharmaceuticals.
The
development
of
synthetic
methodologies
targeting
cyclic
has
attracted
considerable
interest,
given
their
significance
medicinal
chemistry.
These
transformations
can
be
broadly
categorized
into
two
main
types:
(1)
peripheral
modification
(2)
skeletal
remodeling.
Recent
advancements
late-stage
C–H
functionalization
have
showcased
the
potential
strategies.
Conversely,
remodeling,
particularly
through
ring
opening
amines,
emerged
as
a
powerful
approach
to
access
structurally
diverse
amines.
Ring
initiated
by
C–N
bond
cleavage,
predominantly
relies
on
two-electron
mechanisms.
Strained
readily
undergo
such
transformations,
while
those
with
larger-membered
ring,
like
pyrrolidines,
present
greater
challenges.
Oxidative
von
Braun-type
approaches
facilitated
heterolytic
offering
broad
applicability
across
various
In
contrast,
reductive
approaches,
which
enable
homolytic
provide
unique
radical-mediated
transformations.
This
short
review
highlights
recent
progress
single
electron
reduction
induced
ring-opening
methodologies,
focusing
α-aminoketyl
radical
generation
for
selective
amide
cleavage.
Advances
aziridines,
azetidines,
other
are
discussed,
along
implications
future
prospects.
1
Introduction
2
Opening
Aziridines
2.1
Hydrogenation
Alkylation
2.2
Isomerization
2.3
Arylation
3
Azetidines
4
Pyrrolidines
Other
Amines
5
Conclusion
Outlook
Language: Английский
Vitamin B12 and Micellar Solution Enable Regioselective Ring Opening of Epoxides and Aziridines with Electrophilic Olefins
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 23, 2025
Vitamin
B12,
a
water-soluble
cobalt
complex,
is
inherently
predisposed
to
catalyze
reactions
under
aqueous
conditions.
Despite
its
potential,
adopting
this
strategy
for
transformations
of
hydrophobic
reagents
has
been
challenging,
because
their
low
solubility.
Here,
we
demonstrate
that
vitamin
B12
promotes
the
reaction
epoxides
and
aziridines
with
electrophilic
olefins
in
micellar
system.
The
desired
products
are
obtained
efficiently
fully
regioselective
manner.
This
green
catalytic
approach
further
advances
use
sustainable
catalysis
providing
valuable
method
synthesize
important
intermediates.
Language: Английский