Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
11(5)
Published: March 16, 2022
Abstract
Diaminomethylenemalononitrile
organocatalysts
efficiently
promoted
the
asymmetric
direct
vinylogous
conjugate
addition
of
α‐angelica
lactone
to
(
E
)‐
and
Z
)‐benzoyl
acrylonitrile
derivatives.
The
synthesized
products
bear
vicinal
tertiary
quaternary
stereogenic
centers
with
excellent
enantioselectivities
(up
98%
ee).
This
report
is
first
successful
example
stereoselective
using
acrylonitriles
as
Michael
acceptor.
Organic & Biomolecular Chemistry,
Journal Year:
2022,
Volume and Issue:
20(12), P. 2370 - 2386
Published: Jan. 1, 2022
Pyrazolones
and
pyrazoles,
featuring
nitrogen-nitrogen
bonds,
are
two
of
the
most
important
classes
heterocycles,
owing
to
their
widespread
occurrence
in
medicinal
chemistry
functional
materials.
The
last
decade
has
witnessed
a
rapid
increase
construction
chiral
pyrazolone
pyrazole
derivatives,
with
application
derivatives
as
powerful
synthons.
Since
our
review
2018,
large
number
new
achievements
emerged
this
area,
requiring
timely
update.
Thus,
summarizes
these
elegant
based
on
multiple
reactive
sites
different
In
addition,
mechanisms
interesting
biological
investigations
relating
corresponding
products
also
discussed.
Marine Drugs,
Journal Year:
2021,
Volume and Issue:
19(11), P. 645 - 645
Published: Nov. 18, 2021
The
marine
environment
is
an
underexplored
treasure
that
hosts
huge
biodiversity
of
microorganisms.
Marine-derived
fungi
are
a
rich
source
novel
metabolites
with
unique
structural
features,
bioactivities,
and
biotechnological
applications.
Marine-associated
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(45), P. 8348 - 8353
Published: Nov. 10, 2022
A
palladium-catalyzed
enantioselective
α-allylation
of
deconjugated
butenolides
with
aza-π-allylpalladium
1,4-diploes,
in
situ
generated
from
palladium-mediated
decarboxylation
cyclic
carbamates
and
amide-substituted
acyclic
carbonates,
has
been
successfully
developed.
An
array
enantioenriched
2-piperidones
bearing
an
all-carbon
quaternary
stereocenter
were
obtained
high
yields
excellent
enantioselectivities
(up
to
99%
yield
ee).
The
utility
this
method
was
also
showcased
by
a
large-scale
reaction
synthetic
transformations
the
product.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(10), P. 2110 - 2145
Published: Jan. 1, 2021
Conjugated
ynones
are
easily
accessible
feedstock
and
the
existence
of
an
alkyne
bond
endows
with
different
attractive
reactivities,
thus
making
them
unique
substrates
for
catalytic
asymmetric
reactions.
Their
compatibility
under
organocatalytic,
metal-catalyzed
as
well
cooperative
conditions
has
resulted
in
numerous
enantioselective
transformations.
Importantly,
conjugated
can
act
nucleophiles
or
electrophiles,
serve
accessed
synthons
cyclization
pathways.
This
review
summarizes
recent
literature
examples
reactions
related
compounds
such
α-ketoesters,
classifies
these
reaction
types
alongside
mechanistic
insights
whenever
possible.
We
aim
to
trigger
more
intensive
research
future
render
transformation
a
common
reliable
tool
synthesis.
ACS Catalysis,
Journal Year:
2021,
Volume and Issue:
11(22), P. 13921 - 13934
Published: Nov. 2, 2021
Exploring
multistep
cascade
reactions
triggered
by
C–H
activation
are
recognized
as
appealing,
yet
challenging.
Herein,
we
disclose
a
Rh(III)-catalyzed
domino
coupling
of
N-carbamoyl
indoles
and
4-hydroxy-2-alkynoates
for
the
streamlined
assembly
highly
functionalized
furan-2(5H)-ones
in
which
carbamoyl-directing
group
(DG)
is
given
dual
role
an
auxiliary
migrating
acylating
reagent
via
cleavage
stable
C–N
bonds
at
room
temperature.
More
importantly,
obtained
furan-2(5H)-one
skeleton
could
be
further
under
air
situ
C5–H
hydroxylation
simply
switching
solvent
or
additive,
providing
fully
substituted
with
installation
alcohol-based
C5
quaternary
carbon
center.
Detailed
experimental
studies
density
functional
theory
calculations
reveal
that
Rh(III)-mediated
tandem
activation/alkyne
insertion/DG
migration/lactonization
accounts
developed
transformation
to
achieve
high
functionalities
observed
exclusive
selectivity.
The
potential
biological
application
class
potent
PPARγ
ligands
highlights
synthetic
utility
methodology.
This
protocol
endowed
several
salient
features
including
efficient
activation,
excellent
chemo-,
regio-,
stereoselectivity,
bond-forming
efficiency
(e.g.,
two
C–C
C–O
bonds),
solvent-
additive-controlled
product
selectivity,
good
functional-group
compatibility,
mild
redox-neutral
conditions.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(23)
Published: March 22, 2022
γ-Butenolide
and
γ-butyrolactone
scaffolds
are
two
types
of
important
core
structures
in
numerous
natural
products
bioactive
targets.
However,
methods
to
construct
the
chiral
quaternary
arylated
γ-butenolide
rarely
explored.
We
herein
report
an
efficient
Pd-catalyzed
enantioselective
γ-arylation
β,γ-unsaturated
butenolides
with
aryl
bromides,
which
shows
high
γ-selectivity,
good
functional
group
tolerance
excellent
enantioselectivity.
Notably,
this
protocol
also
allows
for
facile
construction
tricyclic
tetrahydroindolines
tetrahydroisoquinolinones
one
step.
DFT
calculations
consistent
experimental
results,
suggesting
that
is
favoured
over
α-arylation.
Finally,
method
applied
rapid
synthesis
product
(R)-(+)-boivinianin
A.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(28)
Published: May 12, 2023
Chiral
heterocycles
with
two
or
more
carbon
stereocenters
are
quite
important
skeletons
in
many
fields.
However,
powerful
strategies
for
the
construction
of
such
synthetically
valuable
heterocycles,
especially
remote
stereocenters,
have
largely
lagged
behind.
We
report
here
a
method
synthesis
chiral
γ-butyrolactones
non-vicinal
from
readily
available
chemical
feedstocks
under
mild
conditions.
Both
diastereoisomers
can
be
obtained
good
to
excellent
enantioselectivities.
The
well-designed
copper/PyBox
catalytic
system
overrides
intrinsic
stereoinduction
close
chirality
center
generated
by
previous
innocent
radical
addition
step.
Nevertheless,
this
work
has
power
selectively
provide
one
single
diastereoisomer
taking
advantage
epimerization
effect
but
also
synthesize
all
four
pair
ligands
L2
and
L2'
having
opposite
chirality.
useful
transformed
into
acyclic
cyclic
molecules
stereocenters.
Mechanistic
studies
reveal
that
reaction
follows
linear
relationship
well
performed
less
loading
amount
ligand
compared
copper
catalyst.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(19), P. 4111 - 4116
Published: May 8, 2024
By
integration
of
oxocarbenium
activation
and
Lewis
acid
coordination
via
conformational
proximity-driven,
Pd(II)-
or
Cu(I)-catalyzed
intramolecular
ketone
haloacylation,
regio-
stereoselective
heterolytic
ring-opening
1,5-haloacylation
cyclopropyl
ketones,
including
those
with
weak
single
alkyl
donors,
has
been
developed
for
the
synthesis
valuable
α-quaternary
halo-γ-butenolides.
The
vicinal
carboxylic
acceptors
are
no
longer
just
spectator
activators.
Further,
this
reaction
delivers
a
constant
regioselectivity
regardless
electronic
nature
substituents,
even
malonate.
New Journal of Chemistry,
Journal Year:
2023,
Volume and Issue:
47(35), P. 16636 - 16642
Published: Jan. 1, 2023
A
general
mechanistic
map
of
the
PPh
3
-catalyzed
transformation
reaction
MBH
carbonate
has
been
theoretically
studied
and
NCI
ELF
analyses
are
performed
to
disclose
origins
selectivities
role
catalyst,
respectively.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Jan. 1, 2024
An
allylation/lactonization
cascade
reaction
for
the
synthesis
of
γ-butenolides
was
developed.
The
is
featured
with
mild
conditions
rapid
completion
within
10
minutes
in
most
cases,
achieving
high
regio-
and
enantioselectivity.
