Catalysts,
Journal Year:
2023,
Volume and Issue:
13(12), P. 1502 - 1502
Published: Dec. 8, 2023
The
glycine
motif
is
widely
prevalent
in
bioactive
peptides.
Thus,
the
direct
and
precise
modification
of
derivatives
has
attracted
significant
attention
over
past
few
decades.
Among
various
protocols
for
derivatives,
visible-light-driven
α-C(sp3)–H
bond
functionalization
emerged
as
a
powerful
tool
to
achieve
this
objective,
owing
its
merits
atom
economy,
selectivity,
reaction
simplicity,
sustainability.
This
review
summarizes
recent
advancements
derivatives.
contents
are
organized
based
on
photocatalysts
employed
modes
process.
mechanism,
challenges
encountered,
future
trends
also
discussed,
enabling
readers
understand
current
developmental
status
field.
European Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 21, 2025
Abstract
A
photoredox‐catalyzed
decarboxylative
C(
sp
3
)−H
alkylation
of
glycine
derivatives,
utilizing
(+)/(−)‐camphorsultam
as
a
chiral
auxiliary
and
alkyl
N
‐hydroxyphthalimide
(NHP)
ester
radical
precursor,
has
been
developed,
providing
an
efficient
approach
for
the
stereoselective
synthesis
valuable
enantioenriched
unnatural
α
‐alkylated
amino
acid
derivatives.
The
methodology
operates
under
mild
conditions,
demonstrates
broad
substrate
tolerance,
exhibits
excellent
stereoselectivity.
Preliminary
mechanistic
investigations
indicate
that
reaction
proceeds
via
pathway.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(7), P. 1072 - 1081
Published: March 17, 2023
Abstract
Being
in
its
infancy,
radical
cross‐coupling
is
highly
efficient
for
C−C
bond
construction,
though
suffers
from
selectivity
problems
and
limited
reaction
types.
New
methodologies
to
realize
selectively
are
desired.
Herein,
an
iron
catalyzed
deconstructive
cyanomethylation
of
unstrained
cyclic
linear
alcohols
with
acetonitrile
has
been
developed
through
cross‐coupling.
The
unprecedented
method
enables
a
ring‐opening
functionalization
cyclohexanols
produce
α‐cyanomethyl
ketones.
Notably,
the
challenging
involves
twice
single
cleavage
β‐scission
alkoxyl
intermediates,
C(
sp
3
)−H
transformation
via
hydrogen
atom
transfer
(HAT)
procedures,
resulting
two
carbon
species
that
process
form
new
)−C(
)
selectively.
α‐arylketo
α‐aryl
substituted
tertiary
can
also
be
applied
as
substrates,
leading
terminal
cyano‐functionalized
products,
ketone
leaving
fragment.
Mechanistically,
procedure
generate
chlorine
in‐situ
formed
intermediate
cycloalkyl
hypochlorite
was
suggested.
magnified
image
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(23), P. 4329 - 4334
Published: June 1, 2023
An
inexpensive
iron-catalyzed
alkoxyl
radical-induced
C–C
bond
cleavage/gem-difluoroalkylation
cascade
is
presented.
Regulated
by
the
structure
of
radical
precursors,
fluorinated
distal
diketones
were
synthesized
through
a
ring-opening
strategy
and
difluoroalkylated
medium-sized
lactones
macrolactones
constructed
via
ring-expansion
strategy.
Both
protocols
proceeded
under
mild
redox
neutral
conditions
with
broad
substrate
scope
good
functional
group
compatibility.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(20), P. 13727 - 13732
Published: May 10, 2024
Although
chemical
methods
for
the
selective
derivatization
of
amino
acid
(AA)
side
chains
in
peptides
and
proteins
are
available,
N-terminal
labeling
is
challenging,
especially
glycine,
which
has
no
chain
at
α-carbon
position.
We
report
here
a
double
activation
glycine's
α-methylene
group
that
allows
this
AA
to
be
differentiated
from
other
19
AAs.
A
condensation
reaction
dibenzoylmethane
with
glycine
results
formation
an
imine,
subsequent
tautomerization
followed
by
intramolecular
cyclization,
leading
fluorescent
pyrrole
ring.
Additionally,
approach
exhibits
compatibility
AAs
possessing
reactive
chains.
Further,
method
pull-down
assays
mixtures
without
prior
knowledge
peptide
distribution.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(9), P. 2301 - 2309
Published: Jan. 1, 2023
A
Cu-catalysed
and
ligand-controlled
glycine
ligation
method
is
developed
for
the
modular
selective
synthesis
of
diverse
CF
3
-containing
amino
acids
dipeptides.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(85), P. 12783 - 12786
Published: Jan. 1, 2023
A
visible-light-induced
aerobic
oxidative
[2+3]
cycloaddition
reaction
between
glycine
derivatives
and
thiiranes
is
achieved
via
a
cooperative
photoredox
catalysis
iron
catalysis.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(33), P. 6955 - 6960
Published: Aug. 13, 2024
Herein,
we
disclose
an
expedient
visible-light-mediated,
organophotoredox-catalyzed
multicomponent
synthesis
of
unnatural
amino
acids
using
a
Katritzky
salt,
glyoxal
derivatives,
and
substituted
anilines.
Mechanistically,
alkyl
radical
is
generated
from
the
salt
via
deaminative
process
that
undergoes
addition
to
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(6), P. 928 - 932
Published: Feb. 2, 2023
A
facile
and
efficient
nickel-catalyzed
C-C
bond
cleavage/phosphorylation
of
various
cycloalkyl
hydroperoxides
was
developed.
This
radical
ring-opening
strategy
provided
practical
access
to
structurally
diverse
distal
ketophosphine
oxides
in
one
pot
through
concurrent
C═O/C-P
formation
with
high
atom
economy
under
mild
room
temperature
base-free
conditions.
