Organic Letters,
Год журнала:
2023,
Номер
25(32), С. 6006 - 6011
Опубликована: Авг. 1, 2023
We
report
an
enantio-
and
diastereodivergent
synthesis
of
enantioenriched
fluorenes
bearing
bis-1,3-nonadjacent
stereocenters
with
broad
substrate
scope
high
enantioselectivity
(up
to
99%
ee)
under
low
catalyst
loading
(0.1
mol
%).
The
key
the
success
this
method
is
pseudo-diastereodivergent
desymmetrization
stereoisomers
meso-epoxides
enabled
by
same
organocatalyst.
Furthermore,
some
chiral
obtained
exhibit
fluorescence
quantum
yields
76.6%),
as
evidenced
photophysical
properties
studies.
Advanced Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 10, 2025
Abstract
Unnatural
α‐amino
acids
are
found
in
a
wide
variety
of
bioactive
compounds
ranging
from
proteins
to
pharmaceutical
agents
materials
science.
As
result,
the
investigation
efficient
and
simple
methods
for
their
synthesis
is
major
purpose
reaction
development.
In
this
study,
it
that
catalyst
based
on
molybdenum,
an
earth‐abundant
transition
metal,
can
facilitate
amination
readily
accessible
α‐hydroxy
esters
afford
N
‐protected
unnatural
acid
high
yield.
This
process
also
enables
enantioselective
amination,
which
proceeds
through
cooperative
catalysis
chiral
molybdenum
complex
with
phosphoric
(CPA),
complements
earlier
procedures
catalytic
important
class
compounds.
The
obtained
protected
ester
products
directly
useful
or
further
utilized
commercially
available
drugs
analogs.
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Март 26, 2025
Synthetic
methods
that
provide
access
to
skeletally
diverse
heterocyclic
motifs
are
poised
accelerate
drug
discovery
and
streamline
the
synthesis
of
advanced
intermediates
materials.
However,
development
such
synthetic
necessitates
leveraging
previously
unexplored
mechanistic
pathways.
We
report
herein
an
efficient
blue
light-emitting
diode
light-induced
reaction
vinyldiazoacetates
quinones
produces
spirocyclic
dihydrofurans,
featuring
synthetically
challenging
oxaspiro[4,5]decane
core
numerous
medicinal
agents,
agrochemicals,
natural
products.
In
a
departure
from
well-established
photochemical
reactivity
diazo
compounds,
these
reactions
do
not
involve
vinylcarbene
formed
by
photolytic
dinitrogen
extrusion.
Instead,
they
result
photoexcitation
quinone
its
triplet
state
with
subsequent
energy
transfer
vinyldiazo
ester.
The
addition
vinylogous
carbon
vinyldiazoacetate
oxygen
affords
diradical
collapses
dihydrofuran
upon
loss
dinitrogen.
A
strain
release-driven
Bro̷nsted
acid-catalyzed
rearrangement
products
unravels
fused
bicyclic
ring
system
equally
medicinally
valuable
chromenes,
enabling
facile
skeletal
diversification
important
motifs.
Organic Letters,
Год журнала:
2024,
Номер
26(29), С. 6214 - 6219
Опубликована: Июль 17, 2024
The
enantioselective
carbene
insertion
into
N-H
bonds
of
anilines
has
been
realized
by
cooperative
catalysis
ruthenium
complexes
and
chiral
phosphoric
acids,
providing
the
expected
α-aryl
glycines
in
moderate
to
good
yields
with
high
enantioselectivity.
Typically,
slightly
modifying
reaction
conditions,
this
approach
allows
bond
be
effective
for
both
α-alkyl
diazoacetates
first
time
enantioselectivity
(up
96%
95%
ee,
respectively).
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(19), С. 13634 - 13644
Опубликована: Сен. 8, 2023
Herein,
we
reported
an
efficient
and
facile
visible-light-induced
3-alkyl
chromone
synthesis
from
easily
accessible
o-hydroxyaryl
enaminones
α-diazo
esters.
In
this
protocol,
excellent
yields
were
obtained
with
a
broad
substrate
scope
at
room
temperature,
tolerating
various
functional
groups.
Of
note
is
that
eco-friendly
methodology
features
catalyst-
additive-free,
mild
reaction
conditions,
simple
operation
procedure,
easy
scale-up,
which
affords
convenient
pathway
for
the
preparation
of
chromones.
Experimental
results
density
theory
(DFT)
computation
analyses
confirm
participation
carbene
species
active
cyclopropane
intermediate.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(14), С. 3498 - 3503
Опубликована: Янв. 1, 2023
A
copper-catalyzed
asymmetric
[4
+
1]
cycloaddition
of
ethynylbenzoxazinones
with
sulfur
ylides
formed
in
situ
by
photoinduced
carbene
transfer
is
reported
to
afford
chiral
indolines
good
efficiency,
enantio-
and
diastereoselectivities.
Organic Letters,
Год журнала:
2023,
Номер
25(27), С. 5038 - 5043
Опубликована: Июнь 29, 2023
An
operationally
simple
Knoevenagel
condensation/asymmetric
epoxidation/domino
ring-opening
esterification
(DROE)
approach
has
been
disclosed
to
successfully
access
a
good
variety
of
(R)-
and
(S)-α-arylglycine
esters
from
commercially
available
aldehydes,
phenylsulfonyl
acetonitrile,
cumyl
hydroperoxide,
anilines,
readily
Cinchona
alkaloid-based
catalysts
using
single
solvent
reaction
vessel.
DFT
calculations
performed
on
the
key
asymmetric
epoxidation
showed
importance
cooperative
H-bonding
interactions
in
affecting
stereocontrol.
Reaction Chemistry & Engineering,
Год журнала:
2024,
Номер
9(6), С. 1313 - 1319
Опубликована: Янв. 1, 2024
Combination
of
artificial
light
and
solar
panel
tracker
for
integrated
two-step
continuous-flow
diazo
generation,
its
utility
in
late-stage
functionalization.
