Organic Letters,
Journal Year:
2023,
Volume and Issue:
26(14), P. 2862 - 2866
Published: Dec. 26, 2023
Palladium-catalyzed
asymmetric
allylic
alkylation
is
a
versatile
method
for
C–C
bond
formation.
Many
established
classes
of
chiral
ligands
can
perform
reactions
enantioselectively,
but
identification
new
ligand
remains
important
future
development
the
field.
We
demonstrate
that
enantiopure
sSPhos,
bifunctional
monophosphine
ligand,
when
used
as
its
tetrabutyl
ammonium
salt,
highly
effective
benchmark
Pd-catalyzed
reaction.
explore
scope
and
limitations
experiments
to
probe
origin
selectivity.
In
contrast
with
previously
explored
using
it
appears
steric
bulk
around
sulfonate
group
responsible
high
enantioselectivity
in
this
case,
rather
than
attractive
noncovalent
interactions.
European Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
26(36)
Published: July 19, 2023
Abstract
An
efficient
strategy
for
asymmetric
trifluoromethylated
allylic
alkylation
of
easily
available
N
‐substituted
glycine
ethyl
esters
with
α
‐(trifluoromethyl)alkenyl
acetates
has
been
developed.
Catalyzed
by
a
[Pd(C
3
H
5
)Cl]
2
/(
R
)‐BINAP,
various
trifluoromethyl‐containing
ester
derivatives
are
afforded
good
yields
and
excellent
enantioselectivities.
The
product
can
be
readily
converted
into
diverse
fluoro‐substituted
species,
which
shows
the
practicability
this
method.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(22), P. 15007 - 15012
Published: Nov. 6, 2023
Herein,
we
report
the
discovery
of
catalytic
asymmetric
conjugated
addition
allylstannanes
to
indol-2-ones
promoted
by
Ni(II)/chiral
N,N′-dioxide.
This
method
enables
stereodivergent
construction
contiguous
quaternary
carbon
centers
(CQCCs),
which
can
be
readily
achieved
a
suitable
combination
chiral
catalyst
with
stereospecific
allylstannanes.
protocol
allows
for
unified
access
all
stereoisomers
3,3-disubstituted
oxindoles
CQCCs
in
good
excellent
enantioselectivities
and
diastereoselectivities.
Nature Communications,
Journal Year:
2023,
Volume and Issue:
14(1)
Published: Dec. 8, 2023
Abstract
The
stereocontrolled
allylic
alkylation
of
carbonyl
compounds
with
the
goal
producing
full
range
stereoisomers
presents
an
effective
approach
for
increasing
productivity
collective
natural
product
synthesis
and
creation
chiral
molecule
libraries
drug
exploration.
simultaneous
control
regio-,
diastereo-,
enantioselectivity
poses
a
significant
synthetic
challenge
in
contemporary
organic
synthesis.
Herein,
we
describe
catalytic
stereodivergent
α-allylation
protocol
applicable
to
both
aliphatic
aromatic
2-acylimidazoles,
thereby
providing
practical
blueprint
divergent
important
building
blocks.
Each
six
isomeric
α-allylated
can
be
readily
obtained
remarkable
yields
exceptional
stereoselectivities,
by
judiciously
selecting
appropriate
leaving
group
permutations
enantiomers
adapted
from
nickel
iridium
catalysts.
versatility
this
asymmetric
has
been
successfully
utilized
enantioselective
(
R
)-arundic
acid
S
,
)-cinamomumolide,
as
well
total
tapentadol.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(47), P. 8397 - 8401
Published: Nov. 20, 2023
We
presented
a
method
for
synthesizing
allylic
chiral
hydrazones
from
1,4-disubstituted
1,3-dienes
and
through
(R)-DTBM-Segphos-Pd(0)-catalyzed
hydrohydrazonation
reaction.
This
transformation
has
wide
range
of
substrates
good
functional
group
tolerance.
The
desired
products
were
obtained
in
medium
to
high
yield
regio-
enantioselectivity.
Synthetic
the
into
various
nitrogen-containing
compounds
was
demonstrated.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
26(14), P. 2862 - 2866
Published: Dec. 26, 2023
Palladium-catalyzed
asymmetric
allylic
alkylation
is
a
versatile
method
for
C–C
bond
formation.
Many
established
classes
of
chiral
ligands
can
perform
reactions
enantioselectively,
but
identification
new
ligand
remains
important
future
development
the
field.
We
demonstrate
that
enantiopure
sSPhos,
bifunctional
monophosphine
ligand,
when
used
as
its
tetrabutyl
ammonium
salt,
highly
effective
benchmark
Pd-catalyzed
reaction.
explore
scope
and
limitations
experiments
to
probe
origin
selectivity.
In
contrast
with
previously
explored
using
it
appears
steric
bulk
around
sulfonate
group
responsible
high
enantioselectivity
in
this
case,
rather
than
attractive
noncovalent
interactions.
