ACS Sustainable Chemistry & Engineering,
Journal Year:
2024,
Volume and Issue:
12(7), P. 2531 - 2537
Published: Feb. 8, 2024
The
process
of
radical
decarboxylation
is
crucial
in
organic
synthesis.
Nevertheless,
dienoic
acids
presents
a
greater
challenge
compared
to
that
aliphatic
carboxylic
acids.
Herein,
catalyst-
and
additive-free
visible-light-promoted
[4
+
3]
annulation
lactones
diamines
was
achieved
via
By
means
this
novel
EDA-activated
annulation,
the
1,5-benzodiazepines,
which
display
wide
range
biological
activities
are
widely
used
many
fields,
can
be
directly
accessed
high
yields
under
mild
conditions.
This
visible-light-induced
tolerates
broad
array
functional
groups
intricate
molecules,
including
pharmaceutical-relevant
compounds
natural
products.
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Aug. 16, 2024
Abstract
The
stereoselective
synthesis
of
β-amino
acids
has
attracted
major
attention
among
the
synthetic
community
in
recent
years.
This
review
provides
an
overview
important
advances
chiral
acid
over
past
decade.
It
covers
development
enantioselective
methods
using
transition-metal
complexes
or
organocatalysts,
mainly
including
catalytic
asymmetric
hydrogenation,
Mannich
reaction,
multicomponent
reactions
diazo
compounds,
and
conjugate
addition.
Additionally,
optically
active
by
other
approaches
are
also
summarized.
1
Introduction
2
Strategies
towards
Asymmetric
Synthesis
β-Amino
Acids
2.1
Hydrogenation
2.2
Reaction
2.3
Conjugate
Addition
2.4
Multicomponent
Reactions
2.5
Miscellaneous
2.5.1
from
Chiral
Amines
2.5.2
Isoxazolidinones
2.5.3
Other
Methodologies
3
Summary
Outlook
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(20), P. 3682 - 3686
Published: May 16, 2023
A
palladium
catalyzed
tandem
reaction
between
ortho-functionalized
aryl
enones
and
2,4-dienyl
carbonates
has
been
presented,
proceeding
through
sequential
2,4-dienylation/Michael
addition/π-σ-π
isomerization/allylic
alkylation.
broad
array
of
enantioenriched
architectures
having
fused
spirocyclic
frameworks
are
constructed
in
moderate
to
excellent
yields
stereoselectivity.
Notably,
the
intrinsic
intramolecular
Diels-Alder
pattern
dienylated
intermediates
is
well
reversed
via
Pd(0)-π-Lewis
base
catalysis.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(36), P. 6649 - 6653
Published: Sept. 1, 2023
A
straightforward
approach
for
the
asymmetric
synthesis
of
multifunctionalized
γ-lactams,
including
those
bearing
two
tetrasubstituted
stereogenic
centers,
has
been
developed
through
a
palladium-catalyzed
vinylogous
addition/allylic
amination
process
between
1,3-dienes
and
α-ketoamides.
This
protocol
features
advantages
ready
substrate
availability,
broad
applicability,
high
efficiency,
excellent
stereoselectivity,
making
it
an
attractive
complementary
tool
to
previous
strategies.
Synthesis,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 30, 2024
Abstract
The
3-substituted-3-hydroxy-2-oxindole
scaffolds
are
not
only
widely
encountered
in
bioactive
compounds
but
also
serve
as
versatile
building
blocks
for
the
construction
of
diverse
valuable
architectures.
Although
numerous
synthetic
methodologies
have
been
developed
over
past
decades,
asymmetric
addition
nucleophiles
or
their
equivalents
to
isatin
substrates
has
proved
be
one
most
efficient
strategies
synthesis
chiral
3-substituted-3-hydroxy-2-oxindoles.
This
Short
Review
aims
summarize
significant
progress
achieved
this
field
recent
years,
with
particular
attention
paid
reaction
development,
mechanism,
and
stereo-induction
models.
1
Introduction
2
Asymmetric
Alkylation
Isatins
3
Alkenylation
Dienylation
4
Alkynylation
5
Allenylation
6
Arylation
7
Annulations
8
Conclusions
Outlooks
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(39), P. 10867 - 10874
Published: Jan. 1, 2023
A
variety
of
deactivated
heteroarenes
tethered
to
an
unsaturated
carbonyl
motif
can
participate
in
asymmetric
Friedel–Crafts
reactions
with
diverse
electrophilic
reagents
catalysed
by
a
chiral
Pd
0
-complex.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
136(6)
Published: Dec. 15, 2023
Abstract
We
report
herein
an
unprecedented
enantioselective
(4+4)
cycloaddition
of
simple
1,3‐dienes
with
azadienes
for
the
construction
fused
eight‐membered
N
‐heterocycles.
In
this
transformation,
π‐Lewis
basic
Pd(0)
catalyst
achieves
activation
to
induce
nucleophilic
addition
followed
by
ring
cyclization
via
a
selective
terminal
allylic
substitution.
Furthermore,
highly
efficient
and
diastereoselective
derivatizations
rings
provide
facile
access
diverse
enantiopure
tetra‐
hexacyclic
compounds
potential
application
in
medicinal
chemistry.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(23)
Published: April 3, 2023
Abstract
σ‐Lewis
base‐catalyzed
regio‐
and
enantioselective
aza‐Morita–Baylis–Hillman
(MBH)
reaction
of
α,β,γ,δ‐unsaturated
systems
remains
a
challenge
due
to
the
intrinsic
covalent
activation
mode.
Here
we
demonstrate
that
Pd
0
complex
can
mediate
dehydrogenative
γ,δ‐unsaturated
compounds
give
corresponding
electron‐poor
dienes,
which
further
undergo
δ‐regioselective
umpolung
Friedel–Crafts‐type
addition
imines
via
auto‐tandem
‐π‐Lewis
base
catalysis.
After
β‐H
elimination
in
situ
formed
II
‐complexes,
unprecedented
chemically
inverse
aza‐MBH‐type
adducts
are
finally
furnished
with
fair
outstanding
enantioselectivity,
diversity
functional
groups
both
ketimine
aldimine
acceptors
be
well
tolerated.
Moreover,
switchable
α‐regioselective
normal
also
realized
by
tuning
catalytic
conditions,
whereas
moderate
good
enantioselectivity
low
excellent
Z
/
E
‐selectivity
is
attained.
Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(44)
Published: Aug. 6, 2024
Abstract
The
transition
metal‐catalyzed
asymmetric
hydro‐functionalization
of
1,3‐dienes
has
been
well
explored,
but
most
reactions
focus
on
electron‐neutral
substrates
in
an
intermolecular
manner.
Here
we
first
demonstrate
that
readily
available
2,4‐dienyl
hydrazones
and
oximes
can
be
efficiently
utilized
the
hydro‐cyclization
reaction
under
co‐catalysis
a
Brønsted
acid
chiral
palladium
complex,
furnishing
multifunctional
dihydropyrazones
dihydroisoxazoles,
respectively.
Diverse
substitution
patterns
for
both
types
electron‐deficient
diene
compounds
are
tolerated,
corresponding
heterocycles
were
generally
constructed
with
moderate
to
excellent
enantioselectivity,
which
elaborated
access
products
higher
molecular
complexity
diversity.
Control
experiments
density
functional
theory
calculations
support
α‐regioselective
protonation
dienyl
by
concurrent
π‐Lewis
base
activation
Pd
0
complex
is
energetically
favoured
formation
active
π‐allylpalladium
intermediates,
outer‐sphere
allylic
amination
or
etherification
mode
adopted
deliver
observed
cyclized
enantioselectively.
