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
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(15), С. 4315 - 4348
Опубликована: Янв. 1, 2021
Catalytic
asymmetric
MCCRs
for
enantioselective
synthesis
of
spirooxindoles
by
using
chiral
phosphoric
acids,
amines,
bifunctional
thiourea/squaramides
and
metal-based
reagents
as
catalysts.
Organic Letters,
Год журнала:
2019,
Номер
21(12), С. 4859 - 4863
Опубликована: Июнь 13, 2019
A
Pd-catalyzed
formal
[5
+
3]
intermolecular
cycloaddition
reaction
of
isatin-derived
α-(trifluoromethyl)imines
with
aryl
substituted
vinylethylene
carbonates
(VECs)
has
been
reported,
affording
trifluoromethyl-group-containing
spirooxindoles
fused
an
eight-membered
ring
as
a
single
diastereoisomer
in
good
yields
the
presence
Brønsted
acid
one-pot
manner
under
mild
conditions.
The
asymmetric
version
this
also
realized
using
chiral
phosphine
ligand
along
further
transformation
obtained
product
to
give
spirooxindolo
pyrrolidine
derivative
upon
oxidation.
Chemistry - An Asian Journal,
Год журнала:
2020,
Номер
15(8), С. 1225 - 1233
Опубликована: Фев. 27, 2020
The
spirooxindole
unit
is
one
of
the
most
widely
investigated
compound
skeletons
existing
in
numerous
natural
and
pharmaceutical
molecules.
Thus,
a
large
number
synthetic
methodologies
have
already
been
reported
to
construct
such
core
structure.
trifluoromethyl
group
another
privileged
organic
chemistry.
introduction
CF3
an
framework
can
significantly
improve
properties
molecule.
In
this
context,
efficient
approach
for
construction
trifluoromethyl-containing
spirooxindoles
becomes
promising
research
direction
among
communities
industry
academia.
Minireview,
recent
advances
summarized
discussed.
addition,
representative
corresponding
reaction
mechanisms
described
as
well.
Advanced Synthesis & Catalysis,
Год журнала:
2019,
Номер
361(9), С. 1923 - 1957
Опубликована: Янв. 9, 2019
Abstract
The
broad
prospects
of
trifluoromethylated
compounds
in
materials
science,
agricultural
chemistry,
and
pharmaceutical
chemistry
have
stimulated
the
rapid
development
asymmetric
organocatalytic
transformations
to
access
these
biologically
important
compounds.
Among
all
types
compounds,
cyclic
with
a
C−CF
3
stereogenic
center
gained
increasing
attention
medicinal
organic
because
they
are
extensively
found
many
active
molecules,
lead
listed
drugs.
This
review
attempts
summarize
developments
synthesis
bearing
since
2012.
magnified
image
Advanced Synthesis & Catalysis,
Год журнала:
2020,
Номер
362(21), С. 4487 - 4512
Опубликована: Сен. 19, 2020
Abstract
Bifunctional
squaramides
as
a
branch
of
organo‐catalysts
showed
powerful
strategies
in
the
art
asymmetric
synthesis,
and
they
have
been
proved
to
be
highly
efficient
versatile
catalysts
for
constructing
complex
molecular
structures
chiral
biologically
active
compounds.
In
this
review,
we
summarized
recent
advances
bifunctional
squaramide‐catalyzed
Mannich
reactions.
magnified
image
The Journal of Organic Chemistry,
Год журнала:
2019,
Номер
84(7), С. 4381 - 4391
Опубликована: Март 13, 2019
An
organocatalyzed
dearomative
aza-Michael/Michael
addition
cascade
of
2-nitrobenzofurans
and
2-nitrobenzothiophenes
with
2-aminochalcones
has
been
developed,
opening
a
new
channel
to
access
series
optically
active
tetrahydrobenzofuro[3,2-b]quinolines
tetrahydrobenzo[4,5]thieno[3,2-b]quinolines
bearing
three
contiguous
stereocenters
excellent
diastereo-
enantioselectivities
(all
cases
>20:1
dr,
up
99%
ee).
This
study
features
the
first
asymmetric
reaction
beginning
aza-Michael
addition.
The
potential
applications
methodology
were
demonstrated
by
preparative-scale
experiment
versatile
transformations
products.
Organic Letters,
Год журнала:
2022,
Номер
24(25), С. 4603 - 4608
Опубликована: Июнь 15, 2022
A
copper-catalyzed
umpolung
of
N-2,2,2-trifluoroethylisatin
ketimines
for
the
enantioselective
1,3-dipolar
cycloaddition
with
benzo[b]thiophene
sulfones
was
developed.
Using
a
catalyst
system
consisting
an
(S,Sp)-tBu-Phosferrox
ligand,
Cu(OTf)2,
and
Cs2CO3,
range
pentacyclic
spirooxindoles
containing
pyrrolidine
benzo[b]sulfolane
subunits
were
obtained
in
high
efficiency
excellent
regio-,
diastereo-,
enantioselectivites
under
mild
conditions.
The
practicality
versatility
reaction
also
demonstrated.
Organic Letters,
Год журнала:
2022,
Номер
24(22), С. 4052 - 4057
Опубликована: Май 27, 2022
With
a
Cu(OTf)2/chiral
ferrocenyl
P,N-ligand
complex
as
catalyst,
the
enantioselective
desymmetrization
of
N-arylmaleimides
was
successfully
realized
by
taking
advantage
asymmetric
1,3-dipolar
cycloaddition
reaction
N-2,2,2-trifluoroethylisatin
ketimines.
A
series
structurally
diverse
F3C-containing
octahydropyrrolo[3,4-c]pyrroles,
bearing
four
contiguous
carbon
stereocenters
and
one
stereogenic
chiral
C-N
axial
bond,
were
obtained
with
excellent
results
(≤99%
yield,
>20:1
dr,
99%
ee).
