Advanced Synthesis & Catalysis,
Год журнала:
2019,
Номер
361(14), С. 3412 - 3419
Опубликована: Апрель 5, 2019
Abstract
A
bifunctional
squaramide‐catalyzed
one‐pot
three‐component
Michael/Mannich‐Michael/cyclization
sequential
cascade
reaction
for
the
construction
of
bispirooxindole‐spirooxindoles
was
developed
in
good
yields
with
excellent
stereoselectivities
(up
to
>20:1
dr,
99%
ee).
series
original
cinnamoyl‐3‐ylideneoxindoles
have
been
applied
this
strategy
first
time.
This
new
provides
a
process
enantioselective
seven
stereocenters,
which
three
are
quaternary
spiro‐stereocenters.
magnified
image
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(46)
Опубликована: Авг. 26, 2022
Stereochemically
defined
organofluorine
compounds
are
vital
to
drug
discovery
and
many
applicable
catalytic
strategies
have
been
introduced
for
accessing
these
entities
stereoselectively.
One
approach
entails
incorporation
of
a
fluorine
atom
(C-F
bond
formation)
or
an
moiety
(e.g.,
CF3
CF2
H),
another
exploits
commercially
available
with
one
more
atoms.
Here,
we
present
the
state-of-the-art
regarding
use
alkenyl
allylic
fluorides
in
preparation
stereochemically
fluoro-organic
molecules.
Allylic
may
be
purchased
generated
from
acid,
carboxylate
salt,
ester,
aldehyde
hydrate,
ketone
bearing
several
atoms
next
carbonyl
group.
We
underscore
untapped
potential
purchasable
compounds,
fluorides,
as
launching
points
development
stereoselective
processes
that
value
therapeutic
science.
The Chemical Record,
Год журнала:
2023,
Номер
23(7)
Опубликована: Янв. 26, 2023
Abstract
Over
the
last
ten
years,
combination
of
organocatalysis
with
transition
metal
(TM)
catalysis
has
become
one
most
important
toolboxes
used
for
synthesizing
optically
pure
compounds
containing
chiral
quaternary
centers,
including
spiro
heterocyclic
molecules.
The
dominant
method
in
enantioselective
synthesis
based
on
synergistic
includes
aminocatalysis
and
NHC
catalysis,
as
already
established
covalent
organocatalytic
strategies.
Another
area
widely
combined
TM
producing
enantiomerically
enriched
is
non‐covalent
dominated
by
phosphoric
acids,
thiourea,
squaramide
derivatives.
This
review
article
aims
to
summarize
methods
constructing
spirocyclic
heterocycles
a
catalysis.
Chemical Science,
Год журнала:
2023,
Номер
14(35), С. 9496 - 9502
Опубликована: Янв. 1, 2023
An
axially
chiral
styrene-based
organocatalyst,
featuring
a
combination
of
structure
and
pyrrole
ring,
has
been
designed
synthesized.
This
catalyst
demonstrates
remarkable
capabilities
in
producing
wide
range
densely
substituted
spirooxindoles
that
feature
an
alkyne-substituted
quaternary
stereogenic
center.
These
are
generated
through
mild
cascade
Michael/cyclization
reactions,
resulting
high
conversion
rates
exceptional
enantioselectivity.
Our
catalytic
model,
based
on
experiments,
X-ray
analysis
DFT
calculations
suggests
matched
π-π
interactions
multiple
H-bonds
between
the
organocatalyst
substrates
play
significant
roles
controlling
stereoselectivity
reaction.
Advanced Synthesis & Catalysis,
Год журнала:
2018,
Номер
361(5), С. 1064 - 1070
Опубликована: Дек. 19, 2018
Abstract
An
efficient
and
practical
organocatalytic
asymmetric
domino
Michael/Mannich
[3+2]
cycloaddition
of
N
‐2,2,2‐trifluoroethylisatin
ketimines
arylidene
azlactones
by
using
a
hydroquinine‐derived
thiourea
as
the
catalyst
has
been
disclosed.
Under
mild
conditions,
broad
range
CF
3
‐containing
3,2’‐pyrrolidinyl
spirooxindole/
dispirooxindole
derivatives
bearing
four
adjacent
stereogenic
centers
including
two
vicinal
spiro
quaternary
chiral
were
obtained
in
high
yields
(up
to
99%
yield)
with
excellent
diastereoselectivities
(>20:1
dr
,
all
case)
enantioselectivities
>99%
ee
).
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2019,
Номер
361(14), С. 3412 - 3419
Опубликована: Апрель 5, 2019
Abstract
A
bifunctional
squaramide‐catalyzed
one‐pot
three‐component
Michael/Mannich‐Michael/cyclization
sequential
cascade
reaction
for
the
construction
of
bispirooxindole‐spirooxindoles
was
developed
in
good
yields
with
excellent
stereoselectivities
(up
to
>20:1
dr,
99%
ee).
series
original
cinnamoyl‐3‐ylideneoxindoles
have
been
applied
this
strategy
first
time.
This
new
provides
a
process
enantioselective
seven
stereocenters,
which
three
are
quaternary
spiro‐stereocenters.
magnified
image
