Angewandte Chemie,
Год журнала:
2024,
Номер
136(46)
Опубликована: Июль 25, 2024
Abstract
An
unprecedented
chemodivergent
strategy
for
parallel
kinetic
resolution
(PKR)
is
disclosed
through
which
two
planar
chiral
products
bearing
different
structures
were
simultaneously
afforded
with
opposite
stereoselectivities.
Two
achiral
esters
are
activated
by
one
single
N‐heterocyclic
carbene
(NHC)
catalyst
to
react
the
enantiomers
of
racemic
imine
substrate
in
a
fashion.
distinct
and
stereoselectivities
respectively
from
same
reaction
system
good
excellent
yields,
enantio‐
diastereoselectivities.
Control
experiments
studies
carried
out
probe
dynamic
properties
during
progress.
The
pyridine
lactam
show
interesting
applications
both
asymmetric
synthesis
pesticide
development.
ACS Catalysis,
Год журнала:
2023,
Номер
13(16), С. 10694 - 10704
Опубликована: Авг. 1, 2023
Developing
diversity-oriented
synthetic
approaches
for
medium-sized
rings
is
of
great
interest,
and
the
divergent
synthesis
with
different
ring
sizes
poses
a
challenging
task.
In
this
study,
we
present
catalyst-controlled
switchable
(5
+
4)/(3
4)
cycloaddition
strategy
seven-
nine-membered
heterocycles.
Utilizing
two
4-aminopyridine
Lewis
base
catalysts,
pyrazole-fused
benzazepines
or
benzoxazonines
can
be
efficiently
assembled
from
same
substrates.
These
products
exhibit
good
stability
without
interconversion
under
reaction
conditions
elevated
temperatures.
The
origin
chemoselectivity
was
elucidated
by
means
computational
studies
involving
DFT
calculations,
distortion/interaction
analysis,
noncovalent
interaction
analysis.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(46)
Опубликована: Июль 25, 2024
Abstract
An
unprecedented
chemodivergent
strategy
for
parallel
kinetic
resolution
(PKR)
is
disclosed
through
which
two
planar
chiral
products
bearing
different
structures
were
simultaneously
afforded
with
opposite
stereoselectivities.
Two
achiral
esters
are
activated
by
one
single
N‐heterocyclic
carbene
(NHC)
catalyst
to
react
the
enantiomers
of
racemic
imine
substrate
in
a
fashion.
distinct
and
stereoselectivities
respectively
from
same
reaction
system
good
excellent
yields,
enantio‐
diastereoselectivities.
Control
experiments
studies
carried
out
probe
dynamic
properties
during
progress.
The
pyridine
lactam
show
interesting
applications
both
asymmetric
synthesis
pesticide
development.
Green Synthesis and Catalysis,
Год журнала:
2022,
Номер
4(2), С. 78 - 88
Опубликована: Дек. 14, 2022
Indanone-containing
compounds
are
very
important
components
of
various
natural
products,
chemical
drugs,
agrochemicals
and
functionalized
material
fields.
1,3-Indanedione
is
a
typical
cyclic
1,3-dicarbonyl
compound
with
three
contiguous
reactive
electrophilic
nucleophilic
sites.
The
easily
prepared
2-arylidene-1,3-indanediones
active
α,β-unsaturated
carbonyl
could
act
as
1,3-dipolarophile,
1,4-dienophile
1-oxa-1,3-diene,
etc.
On
the
other
hand,
homodimer
(bindone)
cyclotrimer
(truxenone)
derived
from
base-catalyzed
self-condensation
1,3-indanedione
also
compounds.
Therefore,
its
derivatives
can
be
employed
key
substrates
in
domino
multicomponent
reactions.
In
this
review,
we
summarized
recent
progress
on
reactions
1,3-indanedione,
especially
our
achievements
synthetic
applications
for
complex
indanone-containing
carbocyclic
heterocyclic
Communications Chemistry,
Год журнала:
2023,
Номер
6(1)
Опубликована: Июнь 19, 2023
Significant
progress
has
been
made
in
asymmetric
synthesis
through
the
use
of
transition
metal
catalysts
combined
with
Lewis
bases.
However,
a
dual
catalytic
system
involving
4-aminopyridine
and
received
little
attention.
Here
we
show
metal/Lewis
base
relay
featuring
silver
acetate
modified
chiral
pyrrolidinopyridine
(PPY).
It
was
successfully
applied
cycloisomerization/(2
+
3)
cycloaddition
reaction
enynamides.
Bispirocyclopentene
pyrazolone
products
could
be
efficiently
synthesized
stereoselective
economical
manner
(up
to
>19:1
dr,
99.5:0.5
er).
Transformations
product
access
stereodivergent
diastereoisomers
densely
functionalized
polycyclic
derivatives.
Mechanistic
studies
illustrated
model
origin
uncommon
chemoselectivity.
In
subsequent
bioassays,
containing
privileged
drug-like
scaffold
exhibited
isoform-selective
phosphodiesterase
1
(PDE1)
inhibitory
activity
vitro.
The
optimal
lead
compound
displayed
good
therapeutic
effect
for
ameliorating
pulmonary
fibrosis
via
inhibiting
PDE1
vivo.
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9322 - 9327
Опубликована: Окт. 24, 2024
The
present
work
develops
a
DMAP-catalyzed
[3
+
2]
cycloaddition
of
vinyl
oxiranes
with
activated
ketone
compounds,
affording
dioxolane
derivatives
moderate
to
excellent
yields.
This
approach
represents
the
first
Lewis
base
(LB)-catalyzed
ring-opening
reaction
epoxides,
simultaneously
providing
rare
oxygen-containing
active
intermediate
in
this
field.
gram-scale
preparation
and
facile
derivatization
cycloadduct
highlight
significant
synthetic
potential
strategy.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(14), С. 10190 - 10198
Опубликована: Июнь 30, 2023
A
novel
DMAP-catalyzed
[4+3]
spiroannulation
of
pyrazolone-derived
Morita-Baylis-Hillman
carbonates
with
N-(o-chloromethyl)aryl
amides
was
developed.
This
reaction
led
to
the
assembly
medicinally
relevant
pyrazolone
and
azepine
nuclei
into
a
structurally
new
spirocyclic
scaffold,
diverse
array
spiro[pyrazolone-azepine]
products
were
afforded
in
good
excellent
yields
(up
93%)
wide
substrate
scope
(23
examples)
under
mild
conditions.
Moreover,
gram-scale
product
transformations
conducted,
which
further
increased
diversity
products.
Chemical Communications,
Год журнала:
2022,
Номер
58(68), С. 9504 - 9507
Опубликована: Янв. 1, 2022
An
organocatalyzed
asymmetric
[3+2]
spiroannulation
reaction
of
pyrazolone-derived
MBH
carbonates
with
alkynyl
ketones
was
described,
affording
chiral
spiro[cyclopentadiene-pyrazolone]
scaffolds
in
good
yields
high
degrees
enantiocontrol.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(10), С. 2252 - 2256
Опубликована: Апрель 5, 2024
Abstract
The
domino
annulation
reactions
of
o
‐aminotrifluoroacetophenone
derivatives
and
MBH
carbonates
enabled
by
PPh
3
have
been
reported,
which
provide
a
series
tetrahydrofuro[3,2‐b]indolines
containing
CF
‐substituted
tetrasubstituted
carbon
stereocenters
in
yields
74
to
95%
>20:1
dr.
In
this
process,
were
used
as
C1/C3
synthons.
MTT
assay
shows
that
the
products
exhibit
activity
inhibitory
effect
on
proliferation
Hela
cancer
cell
line.
