ACS Catalysis,
Год журнала:
2024,
Номер
14(3), С. 1505 - 1513
Опубликована: Янв. 16, 2024
The
regio-
and
diastereoselective
alkene
isomerization
hydrofunctionalization
sequence
enabled
by
transition-metal
complexes
allows
rapid
activation
assembly
of
the
C(sp3)–H
bond
that
is
either
adjacent
or
distal
to
initial
double
bond,
which
has
been
a
longstanding
challenge
in
this
field.
Herein,
we
develop
unusual
rhodium-catalyzed
alkylidenecyclobutanes
with
subsequent
hydroacylation
reaction
provide
multisubstituted
cyclobutanes
continuous
stereocenters.
Note
tandem
process
features
good
diastereoselectivity
profile.
Isotopic
labeling
experiments
support
"exo
endo"
migration
coordinated
cyclobutene
responsible
for
deuterium
incorporation
observed
cyclobutane
product.
Green Chemistry,
Год журнала:
2022,
Номер
24(6), С. 2542 - 2556
Опубликована: Янв. 1, 2022
An
air-stable,
recyclable,
and
sustainable
copper
catalyst
was
efficiently
utilized
for
the
aerobic
oxidation
of
biomass
model
compound
vanillyl
alcohol
to
important
aroma
vanillin
under
green
conditions.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(34)
Опубликована: Июнь 30, 2023
Chain
walking
has
been
an
efficient
route
to
realize
the
functionalization
of
inert
C(sp3
)-H
bonds,
but
this
strategy
is
limited
mono-olefin
migration
and
functionalization.
Herein,
we
demonstrate
feasibility
tandem
directed
simultaneous
migrations
remote
olefins
stereoselective
allylation
for
first
time.
The
adoption
palladium
hydride
catalysis
secondary
amine
morpholine
as
solvent
critical
achieving
high
substrate
compatibility
stereochemical
control
with
method.
protocol
also
applicable
three
vicinal
bonds
thus
construct
continuous
stereocenters
along
a
propylidene
moiety
via
short
synthetic
process.
Preliminary
mechanistic
experiments
corroborated
design
dienes.
Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(34), С. 18722 - 18730
Опубликована: Авг. 15, 2023
Selective
transformation
of
alkyne
triple
bonds
to
double
serves
as
an
efficient
platform
construct
substituted
alkenes.
While
significant
advances
have
been
made
in
its
spatiotemporal
regulation,
achieving
a
multicomponent
enantioselective
reaction
that
requires
multifaceted
selectivity
issues
be
overcome
is
still
uncommon.
Here,
we
report
unprecedented
asymmetric
anti-stereoselective
borylcarbofunctionalization
terminal
alkynes
by
nickel
catalysis.
The
utilization
inexpensive
chiral
diamine
ligand
enables
the
three-component
cross-coupling
alkynes,
diboron
reagent,
and
prochiral
alkyl
electrophiles
with
high
levels
regio-,
stereo-,
enantioselectivities.
This
provides
protocol
access
enantioenriched
alkenyl
esters
bearing
α-stereogenic
center,
remarkably
practical,
has
broad
scope
outstanding
functional
group
compatibility.
In
addition,
value
this
method
highlighted
diversity
follow-up
stereoretentive
derivatizations
stereoselective
concise
synthesis
complex
drug
molecules.
ACS Catalysis,
Год журнала:
2024,
Номер
14(3), С. 1505 - 1513
Опубликована: Янв. 16, 2024
The
regio-
and
diastereoselective
alkene
isomerization
hydrofunctionalization
sequence
enabled
by
transition-metal
complexes
allows
rapid
activation
assembly
of
the
C(sp3)–H
bond
that
is
either
adjacent
or
distal
to
initial
double
bond,
which
has
been
a
longstanding
challenge
in
this
field.
Herein,
we
develop
unusual
rhodium-catalyzed
alkylidenecyclobutanes
with
subsequent
hydroacylation
reaction
provide
multisubstituted
cyclobutanes
continuous
stereocenters.
Note
tandem
process
features
good
diastereoselectivity
profile.
Isotopic
labeling
experiments
support
"exo
endo"
migration
coordinated
cyclobutene
responsible
for
deuterium
incorporation
observed
cyclobutane
product.
