Organic Letters,
Год журнала:
2024,
Номер
26(7), С. 1447 - 1451
Опубликована: Фев. 14, 2024
Difluoroenoxysilane,
a
commonly
used
difluoroallylating
reagent,
has
attracted
considerable
attention
in
recent
years.
However,
its
application
the
annulation
reaction
for
construction
of
fluorinated
heterocyclic
compounds
remains
relatively
limited.
Presented
here
is
Brønsted
acid-catalyzed
efficient
formal
[4
+
2]
difluoroenoxysilanes
with
α-cyano
chalcones.
The
developed
protocol
demonstrates
tolerance
to
various
substituents
under
mild
conditions,
providing
reliable
approach
construct
gem-difluoro-3,4-dihydro-2H-pyrans
good
excellent
yields
high
diastereoselectivities.
ACS Catalysis,
Год журнала:
2022,
Номер
12(24), С. 15750 - 15757
Опубликована: Дек. 7, 2022
A
photochemical
synthesis
of
brominated
α,α-difluoro-γ-lactones
from
cinnamyl
alcohols
and
ethyl
bromodifluoroacetate
is
reported
via
one-pot
Giese
addition/lactonization/halogen-atom
transfer
(XAT)
processes.
This
transformation
provides
in
moderate
to
good
diastereoselectivities.
The
reaction
affords
a
rapid
increase
molecular
complexity
organofluorine
chemical
space.
Dispersion-corrected
density
functional
theory
(DFT)
calculations
experiments
support
lactonization-induced
radical
chain
mechanism
which
long-lived
intermediate
undergoes
diastereoselective
halogen-atom
restart
the
cycle.
Advanced Synthesis & Catalysis,
Год журнала:
2023,
Номер
365(10), С. 1678 - 1684
Опубликована: Апрель 28, 2023
Abstract
A
feasible
and
umpolung
strategy
for
the
synthesis
of
structurally
diverse
β
‐amino
ketones
has
been
achieved
through
TEMPO
mediated
C−N
coupling
cyclopropanols
with
nitrogen
nucleophiles.
Mechanism
studies
indicated
that
in
situ
generated
enones
derived
from
are
key
intermediates
play
multiple
roles,
including
radical
initiator,
trapping
reagent,
a
porter
‐hydrogen
an
base.
This
protocol
features
broad
substrate
scope,
good
scalability
to
excellent
yields
provides
alternative
complementary
approach
important
ketone
scaffolds
under
metal
additive‐free
conditions.
magnified
image
Organic Letters,
Год журнала:
2023,
Номер
25(47), С. 8445 - 8450
Опубликована: Ноя. 17, 2023
Despite
the
widespread
presence
of
chiral
cyclopentane
motif,
asymmetric
synthesis
cyclopentanes
containing
five
stereocenters
remains
a
formidable
challenge.
Here,
we
present
an
N-heterocyclic
carbene
(NHC)-catalyzed
cascade
reaction
enal
and
oxindole-dienone,
which
allows
access
to
spiroxindole
featuring
complete
set
centers
on
five-membered
carbocycle.
This
strategy,
characterized
by
formation
multiple
bonds
centers,
demonstrates
broad
substrate
scope,
exclusive
diastereoselectivity,
up
99:1
er.
Organic Letters,
Год журнала:
2023,
Номер
25(34), С. 6368 - 6373
Опубликована: Авг. 18, 2023
A
chemo-,
regio-,
and
stereoselective
reaction
of
trifluoromethyl
enones,
phenylsilane,
phosphine
oxides
through
a
sequential
hydrodefluorination
defluorophosphorylation
relay
is
developed
for
the
synthesis
distinctive
gem-fluorophosphine
alkenes.
This
multicomponent
occurred
under
transition-metal-free
conditions
with
good
functional
group
tolerance.
Moreover,
preinstalled
carbonyl
auxiliary
important
tuning
reactivity
β-trifluoromethyl
thereby
enabling
controllable
selective
functionalization
two
fluorine
atoms
in
trifluoromethylated
enones.
Organic Letters,
Год журнала:
2024,
Номер
26(7), С. 1447 - 1451
Опубликована: Фев. 14, 2024
Difluoroenoxysilane,
a
commonly
used
difluoroallylating
reagent,
has
attracted
considerable
attention
in
recent
years.
However,
its
application
the
annulation
reaction
for
construction
of
fluorinated
heterocyclic
compounds
remains
relatively
limited.
Presented
here
is
Brønsted
acid-catalyzed
efficient
formal
[4
+
2]
difluoroenoxysilanes
with
α-cyano
chalcones.
The
developed
protocol
demonstrates
tolerance
to
various
substituents
under
mild
conditions,
providing
reliable
approach
construct
gem-difluoro-3,4-dihydro-2H-pyrans
good
excellent
yields
high
diastereoselectivities.
