Angewandte Chemie,
Год журнала:
2022,
Номер
134(46)
Опубликована: Авг. 26, 2022
Abstract
Stereochemically
defined
organofluorine
compounds
are
vital
to
drug
discovery
and
many
applicable
catalytic
strategies
have
been
introduced
for
accessing
these
entities
stereoselectively.
One
approach
entails
incorporation
of
a
fluorine
atom
(C−F
bond
formation)
or
an
moiety
(e.g.,
CF
3
2
H),
another
exploits
commercially
available
with
one
more
atoms.
Here,
we
present
the
state‐of‐the‐art
regarding
use
alkenyl
allylic
fluorides
in
preparation
stereochemically
fluoro‐organic
molecules.
Allylic
may
be
purchased
generated
from
acid,
carboxylate
salt,
ester,
aldehyde
hydrate,
ketone
bearing
several
atoms
next
carbonyl
group.
We
underscore
untapped
potential
purchasable
compounds,
fluorides,
as
launching
points
development
stereoselective
processes
that
value
therapeutic
science.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
9(3), С. 810 - 815
Опубликована: Дек. 20, 2021
The
palladium-catalyzed
asymmetric
trifluoromethylated
allylic
alkylation
of
3-substituted
oxindoles
using
α-(trifluoromethyl)alkenyl
acetates
as
trifluoromethyl-containing
allyl
precursors
was
developed.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(19), С. 13645 - 13654
Опубликована: Сен. 8, 2023
A
copper/PyBisulidine-catalyzed
enantioselective
alkynylation
of
electrophilic
pyrazole-4,5-dione
with
terminal
alkynes
has
been
developed.
Chiral
tertiary
propargylic
alcohols
bearing
the
pyrazolone
motif
were
prepared
yields
(up
to
99%)
and
enantioselectivities
99%
ee).
The
prominent
feature
this
protocol
includes
its
mild
reaction
conditions
good
stereoselectivities.
nonlinear
effect
study
showed
that
catalytically
active
specie
was
a
monomeric
catalyst
excess
copper
activated
through
π-system.
Organic Letters,
Год журнала:
2024,
Номер
26(35), С. 7318 - 7323
Опубликована: Авг. 26, 2024
In
this
paper,
we
developed
a
highly
enantioselective
alkylation
of
4-substituted
pyrazolones
catalyzed
by
phase-transfer
catalysis.
Cheap
halohydrocarbons
were
employed
as
electrophilic
alkylationg
agents,
and
propargyl,
allyl,
benzyl
products
with
all-carbon
quaternary
stereocenters
afforded
excellent
enantioselectivities
good
yields.
We
found
that
the
unique
structures
catalyst
(hydrogen
bond
donors
C-9
hydroxyl
group
amide
group,
triphenyl
at
NH-position)
important
for
enantioselectivity.
Furthermore,
chiral
propargyl
could
be
easily
connected
to
azide
molecules
click
cycloaddition,
which
offers
opportunities
obtain
structurally
diverse
pyrazolones.
Chemical Communications,
Год журнала:
2024,
Номер
unknown
Опубликована: Янв. 1, 2024
A
hitherto
unknown
cross-conjugated
vinylogous
anionic
annulation
of
π-CF
3
-allyl
Pd-complexes
with
4-methyl-3-trifluoroacetyl
quinolones
has
been
disclosed
to
access
the
diversely
functionalized
phenanthridones.
This
paper
describes
an
iridium-catalyzed
allylation
of
ring-fused
pyrazolones
that
proceeds
with
excellent
regio-,
diastereo-
and
enantio-selectivities.
The
approach
exploits
unactivated,
racemic
allylic
alcohols
as
a
source
allyl
building
blocks.
Asymmetric
syntheses
series
biologically
relevant,
chiral
highlight
the
utility
methodology.
use
Cu(OTf)
Organic & Biomolecular Chemistry,
Год журнала:
2021,
Номер
19(38), С. 8241 - 8245
Опубликована: Янв. 1, 2021
Highly
regio-
and
stereoselective
ortho
-vinylation
of
β-naphthols
has
been
accomplished
via
CF
3
–π-allyl
Pd-complex
for
the
first
time.
Next,
one-pot
synthesis
-naphtho[2,1-
b
]furans
is
developed
through
a
oxidative
radical
cyclization
reaction.
Synthesis,
Год журнала:
2024,
Номер
56(20), С. 3220 - 3232
Опубликована: Июль 4, 2024
Abstract
A
new
strategy
for
the
asymmetric
allylic
alkylation
of
azlactones
with
α-(trifluoromethyl)allyl
acetates
catalyzed
by
Pd(OAc)2/(R)-BINAP
is
designed
and
developed,
providing
access
to
unsaturated
α-quaternary
α-amino
acid
derivatives
bearing
a
trifluoromethyl
group
contiguous
quaternary
tertiary
stereogenic
centers.
The
products
are
obtained
in
good
yields
exclusive
regioselectivity
excellent
stereoselective
control
under
relatively
mild
reaction
conditions.
scale-up
experiment
shows
no
loss
reactivity
or
stereoselectivity.
synthetic
utility
current
demonstrated
through
transformations
representative
product
afford
several
potentially
bioactive
species.
