Abstract
A
squaramide‐catalyzed
asymmetric
Michael/cyclization
tandem
reaction
between
3‐hydroxychromenones
and
isatylidenemalononitriles
was
developed.
Using
this
strategy,
a
wide
scope
of
spiro[indoline‐3,4′‐pyrano[3,2‐b]chromene]
derivatives,
which
combined
chromone,
pyran,
indolone
in
one
molecule,
could
be
obtained
moderate
to
excellent
yields
(up
94
%)
with
enantioselectivities
95
%
ee).
In
addition,
the
scaled‐up
experiment
also
confirmed
synthetic
practicality
strategy.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(12), С. 2370 - 2386
Опубликована: Янв. 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.
Chemistry - An Asian Journal,
Год журнала:
2020,
Номер
15(18), С. 2838 - 2853
Опубликована: Июль 24, 2020
Abstract
Benzothiophene,
benzofuran,
indole,
and
indene
derivatives
are
privileged
heterocyclic
motifs.
These
present
in
a
wide
range
of
bioactive
natural
products
pharmaceutical
drugs
the
subject
materials
science
research.
However,
construction
benzothiophene,
frameworks
have
been
long‐standing
challenges
to
organic
chemists.
In
this
review,
we
classify
four
structures
synthesized
from
2‐benzylidene‐1‐benzofuran‐3‐one
their
analogues
terms
ring
size
(from
three‐
ten‐membered)
type
(fused
or
spiro),
as
well
summarizing
developments
field.
Finally,
discuss
opening
1,4‐addition
reactions.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(17), С. 4583 - 4590
Опубликована: Янв. 1, 2022
In
this
paper,
a
coupling
partner-dependent
unsymmetrical
C–H
functionalization
of
N
-phenoxyacetamides
leading
to
the
formation
sophisticated
spirocyclic
scaffolds
is
presented.
Molecules,
Год журнала:
2023,
Номер
28(3), С. 1056 - 1056
Опубликована: Янв. 20, 2023
With
a
dinuclear
zinc-ProPhenol
complex
as
catalyst,
an
efficient
and
novel
[3
+
3]
annulation
of
indoline-2-thiones
isatylidene
malononitriles
has
been
successfully
developed
via
the
Brønsted
base
Lewis
acid
cooperative
activation
model.
This
practical
methodology
gives
access
to
broad
range
chiral
spiro[indoline-3,4′-thiopyrano[2,3-b]indole]
derivatives
in
good
yields
with
excellent
levels
enantioselectivities
(up
88%
yield
99%
ee).
Chemical Communications,
Год журнала:
2022,
Номер
58(35), С. 5363 - 5366
Опубликована: Янв. 1, 2022
A
catalytic
asymmetric
construction
of
the
bispiro[pyrazolone-dihydropyrrole-oxindole]
skeleton
catalyzed
by
chiral
DMAP-derived
catalyst
was
successfully
achieved
employing
recently
explored
pyrazolone-derived
MBH
carbonate
in
high
yields
with
excellent
stereoselectivities.
The
proposed
transition
state
indicated
that
intermolecular
hydrogen
bonds
and
π-π
interactive
forces
played
an
essential
role
stereoselective
chemical
transformation.
Molecules,
Год журнала:
2025,
Номер
30(9), С. 2000 - 2000
Опубликована: Апрель 30, 2025
An
efficient
stereoselective
strategy
for
the
synthesis
of
chiral
bisspiro
barbituric
acid–oxindole
derivatives
was
developed.
The
asymmetric
Michael
addition/cyclization
tandem
reaction
between
benzylidene
acids
and
oxindolylmalonitriles
catalyzed
by
squaramide
catalyst,
corresponding
spirocyclic
products
were
obtained
in
good-to-high
yields
(up
to
97%)
with
excellent
stereoselectivities
>99%
ee,
>20:1
dr).
At
same
time,
practicality
verified
gram-scale
preparation
reaction.
