Organic Letters,
Год журнала:
2024,
Номер
26(38), С. 8121 - 8127
Опубликована: Сен. 16, 2024
We
developed
an
organophotoredox
catalytic
system
to
facilitate
the
decarboxylative
allylation
coupling
process
concerning
α-amino
acids
and
related
C-terminal
carboxylate
peptides
using
Morita-Baylis-Hillman
adducts
as
allylic
precursors.
This
metal-free
method
operates
under
mild
conditions
is
compatible
with
various
amino
acids.
The
versatility
of
this
protocol,
particularly
in
chemical
biology
research,
has
been
preliminarily
demonstrated
through
ligation
bioactive
peptide
chains.
The
asymmetric
catalytic
[3+2]
cycloannulation
of
benzoxazinones
with
isatin-derived
ketimines
for
the
efficient
construction
imidazo[5,1-c]oxazinones
has
been
developed,
which
realized
first
reaction
excellent
stereoselectivities.
A
series
containing
three
stereogenic
centers
one
gem-diamine-type
spiro
tetrasubstituted
center
were
obtained
in
this
organocatalytic
good
yields
and
high
functional
group
tolerance.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 7, 2025
Herein,
we
report
an
efficient,
organophotocatalyzed
decarboxylative
(amino)alkylation
of
azomethine
imines
using
readily
available
carboxylic
acids
as
alkylating
agents.
This
transformation
exhibits
wide
scope,
and
a
variety
acids,
including
glycine
derivatives,
were
employed
radical
precursors.
The
use
4CzIPN
the
photocatalyst
allowed
application
nonbenzylic
secondary
tertiary
also,
overcoming
previous
limitations.
applicability
nonprefunctionalized
precursors,
mild
conditions
are
highlights
this
method.
intermediacy
key
intermediates
was
established
by
trapping
experiments.
Abstract
In
this
study,
we
report
an
innovative
development
of
a
visible
light‐induced
synthesis
trifluoromethyl
indoles.
This
novel
methodology
not
only
obviates
the
need
for
traditional
catalysts
but
also
harnesses
energy
photons
to
selectively
introduce
groups
into
indole
substrates.
Leveraging
inexpensive,
easily
handled,
and
non‐toxic
Langlois
reagent
(CF
3
SO
2
Na)
as
CF
source,
in
conjunction
with
light
tert
‐butyl
hydrogen
peroxide
(TBHP),
facilitates
direct
C─H
trifluoromethylation
The
mechanistic
pathway
reaction
is
predicted
help
density
functional
theory
(DFT)
calculations
at
(U)B3LYP/6–31++G(d,p)/SMD/acetonitrile
level
theory.
Organic Letters,
Год журнала:
2024,
Номер
26(38), С. 8121 - 8127
Опубликована: Сен. 16, 2024
We
developed
an
organophotoredox
catalytic
system
to
facilitate
the
decarboxylative
allylation
coupling
process
concerning
α-amino
acids
and
related
C-terminal
carboxylate
peptides
using
Morita-Baylis-Hillman
adducts
as
allylic
precursors.
This
metal-free
method
operates
under
mild
conditions
is
compatible
with
various
amino
acids.
The
versatility
of
this
protocol,
particularly
in
chemical
biology
research,
has
been
preliminarily
demonstrated
through
ligation
bioactive
peptide
chains.
