Asian Journal of Organic Chemistry,
Год журнала:
2022,
Номер
11(12)
Опубликована: Окт. 1, 2022
Abstract
An
efficient,
metal‐free
oxidation
method
of
the
N
‐
ortho
C(sp
3
)−H
bond
amide
via
visible‐light
irradiation
has
been
developed.
A
broad
range
imides
can
be
facilely
obtained
at
room
temperature
and
this
protocol
is
showcased
in
gram‐scale
synthesis.
Preliminary
mechanistic
studies
revealed
that
a
hydrogen
atom
transfer
(HAT)
process
was
involved
H
2
O
offered
main
oxygen
source
to
achieve
greener
photochemical
oxidation.
Organic Letters,
Год журнала:
2025,
Номер
27(4), С. 1054 - 1059
Опубликована: Янв. 16, 2025
Here,
we
present
a
three-component
successive
radical
addition
strategy
for
the
preparation
of
complex
noncanonical
α-amino
acids
from
easily
available
glycine
derivatives,
alkenes,
and
aryl
sulfonium
salts
via
copper-catalyzed
photoredox-neutral
catalytic
cycle.
The
utility
this
method
is
further
demonstrated
by
its
application
in
late-stage
site-selective
modifications
residues
short
peptides.
It
worth
noting
that
only
1
mol
%
copper
catalyst
required
reaction,
demonstrating
high
efficiency.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(6), С. 4056 - 4066
Опубликована: Март 7, 2024
An
organo-photoredox
catalyzed
gem-difluoroallylation
of
glycine
with
α-trifluoromethyl
alkenes
via
direct
C(sp3)–H
functionalization
and
C–F
bond
activation
has
been
described.
As
a
consequence,
broad
range
gem-difluoroalkene-containing
unnatural
amino
acids
are
afforded
in
moderate
to
excellent
yields.
This
reaction
exhibits
multiple
merits
such
as
readily
available
starting
materials,
substrate
scope,
mild
conditions.
The
feasibility
this
highlighted
by
the
late-stage
modification
several
peptides
well
improved
vitro
antifungal
activity
compound
3v
toward
Valsa
mali
compared
that
commercial
azoxystrobin.
Abstract
Sulfur‐containing
amino
acids
and
peptides
play
critical
roles
in
organisms.
Thiol‐ene
reactions
between
the
thiol
residues
of
L
‐cysteine
alkenyl
fragments
designed
coupling
partners
serve
as
primary
tools
for
constructing
C─S
bonds
synthesis
unnatural
sulfur‐containing
acid
derivatives.
These
are
favored
due
to
preference
hydrogen
transfer
from
β‐sulfanyl
carbon
radical
intermediates.
In
this
paper,
study
proposes
utilizing
carbon‐centered
radicals
stabilized
by
capto‐dative
effect,
generated
under
photocatalytic
conditions
N
–aryl
glycine
The
aim
is
compete
with
hydrogen,
enabling
C─C
bond
formation
radicals.
This
protocol
robust
presence
air
water,
offers
significant
potential
a
modular
efficient
platform
synthesizing
modifying
peptides,
particularly
abundant
disulfides
styrenes.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(45)
Опубликована: Сен. 8, 2022
Abstract
Unnatural
amino
acids
are
important
scaffolds
for
novel
drug
candidates,
and
especially
α‐alkyl
have
emerged
as
a
valuable
variant.
This
is
due
to
the
ubiquity
of
alkyl
groups,
which
pervasive
key
motifs
in
natural
products,
biological
pharmaceutical
molecules.
The
development
radical‐based
approaches
organic
synthesis
has
expanded
dramatically
recent
years.
It
enabled
site‐
region‐specific
installation
variety
functionalities
small
molecules,
been
spontaneously
applied
preparation
versatile
acid
building
blocks.
glycine
motif
backbone
gained
significant
attention
allowing
access
complex
α‐unnatural
via
radical‐mediated
α‐C−H
alkylation.
review
summarizes
last
decade's
alkylation
derivatives
provide
unnatural
α‐amino
acids.
advantages,
current
limitations,
perspectives
glycine‐based
also
discussed.
Organic Letters,
Год журнала:
2022,
Номер
24(36), С. 6653 - 6657
Опубликована: Сен. 1, 2022
Switchable
in
situ
SO2
capture
and
CF3
migration
of
enol
triflates
with
peroxyl
compounds
under
iron
catalysis
are
presented.
By
regulating
the
structure
peroxides,
a
variety
keto-functionalized
dialkyl
sulfones
α-trifluoromethyl
ketones
were
selectively
synthesized
good
yields
mild
conditions.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(41), С. 8364 - 8371
Опубликована: Янв. 1, 2023
A
Ce(III)-catalyzed,
visible-light
induced
aerobic
oxidative
dehydrogenative
coupling
reaction
between
glycine
derivatives
and
electron-rich
arenes
is
disclosed.
The
protocol
proceeds
efficiently
under
mild
conditions,
providing
an
efficient
method
for
the
rapid
synthesis
of
α-arylglycine
without
need
external
photosensitizer
additional
oxidant.
Moreover,
this
could
be
performed
on
a
5
mmol
scale,
obvious
reduction
efficiency.
Chemical Communications,
Год журнала:
2023,
Номер
59(18), С. 2628 - 2631
Опубликована: Янв. 1, 2023
A
Ce(III)-catalyzed,
visible-light-induced
aerobic
oxidative
dehydrogenative
coupling/aromatization
reaction
between
glycine
derivatives
and
alkenes
has
been
developed,
which
provides
an
efficient
approach
for
the
synthesis
of
quinoline
post-modification
oligopeptides
containing
residues
under
mild
conditions
without
need
external
photosensitizers.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(3), С. 1657 - 1668
Опубликована: Янв. 19, 2024
Herein,
we
report
a
heterogeneous
visible
light-driven
preparation
of
α-alkylated
glycine
derivatives.
This
approach
employed
β-ketoenamine-linked
covalent
organic
framework
(2D-COF-4)
as
the
photocatalyst
and
N-hydroxy
phthalimide
(NHPI)
esters
alkyl
radical
sources.
Numerous
derivatives,
including
dipeptides,
were
precisely
efficiently
alkylated
under
reaction
conditions.
Based
on
excellent
photoactivity
compatibility
2D-COF-4,
this
alkylation
could
proceed
flexibly
in
green
solvent
(ethanol)
without
any
other
additives.
The
fruitfully
recycled
with
simple
workup
procedure,
revealing
high
ecoscale
value
low
environmental
factor
(E-factor).
