Chemical Communications,
Год журнала:
2022,
Номер
58(21), С. 3493 - 3496
Опубликована: Янв. 1, 2022
An
efficient
and
concise
strategy
has
been
successfully
developed
for
merging
spiro-tetrahydroquinoline
with
spiro-benzofuranone
into
a
single
new
skeleton
through
asymmetric
catalytic
cascade
reactions
catalyzed
by
quinine-derived
chiral
bifunctional
squaramide
organocatalysts.
In
this
approach,
differently
substituted
derivatives
were
smoothly
obtained
high
yields,
excellent
diastereoselectivities
enantioselectivities
(up
to
99%
yield,
up
>20
:
1
dr,
>99%
ee,
40
examples)
under
mild
reaction
conditions.
Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(16)
Опубликована: Фев. 17, 2022
Abstract
We
present
herein
a
highly
efficient
atroposelective
synthesis
of
axially
chiral
1,1′‐bipyrroles
bearing
an
N−N
linkage
from
simple
hydrazine
and
1,4‐diones.
Further
product
derivatizations
led
to
bifunctional
compounds
with
high
potential
in
asymmetric
catalysis.
For
this
chrial
phosphoric
acid
(CPA)‐catalyzed
double
Paal–Knorr
reaction,
intriguing
Fe(OTf)
3
‐induced
enantiodivergence
was
also
observed.
Abstract
Palladium‐catalyzed
decarboxylative
cycloadditions
have
emerged
as
highly
effective
methods
for
constructing
structurally
diverse
carbo‐
and
heterocycles
because
of
the
formation
at
least
two
carbon‐carbon
or
carbon‐heteroatom
bonds
in
a
single
step.
It
is
great
interest
to
chemists
that
this
type
cycloaddition
reactions
possesses
some
special
advantages
such
high
reactivity,
exclusive
regioselectivity,
good
functional
group
compatibility.
Based
on
these
qualities,
palladium‐catalyzed
present
strong
ability
synthetic
chemistry
been
flourished
especially
last
five
years.
In
review,
achievements
involving
cyclic
carbonates,
carbamates,
lactones
accessing
oxacyclo‐,
azacyclo‐
carbocyclic
compounds
are
addressed.
Mechanistic
insights
applications
toward
synthesis
natural
products
discussed.
The
challenges
opportunities
field
also
outlined.
Chemical Science,
Год журнала:
2023,
Номер
14(11), С. 3024 - 3029
Опубликована: Янв. 1, 2023
Inspired
by
a
fungicide,
we
designed
5-vinyloxazolidine-2,4-diones
as
new
precursors
of
π-allylpalladium
zwitterionic
intermediates
and
developed
palladium-catalyzed
asymmetric
(5
+
3)
cycloaddition
with
azomethine
imines
(3
2)
1,1-dicyanoalkenes.
Both
reactions
proceeded
smoothly
under
mild
reaction
conditions
to
produce
various
chiral
heterocyclic
compounds
in
high
yields
excellent
enantioselectivities.
These
results
revealed
that
were
type
suitable
precursor
for
palladium
catalysis
will
find
extensive
applications
Pd-catalyzed
such
allylic
alkylation.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(16), С. 4539 - 4545
Опубликована: Янв. 1, 2024
Rapid
access
to
diverse
spiro[benzofuran-2,2′-bicyclo[2.1.1]hexanes]
via
BF
3
·Et
2
O-catalyzed
[2π
+
2σ]
cycloaddition
of
bicyclo[1.1.0]butanes
with
readily
available
benzofuran-derived
oxa(aza)dienes.
Organic Letters,
Год журнала:
2024,
Номер
26(8), С. 1589 - 1594
Опубликована: Фев. 22, 2024
This
study
demonstrates
a
highly
efficient
regiodivergent
ligand-controlled
palladium-catalyzed
cycloaddition
reaction
of
vinyloxazolidine-2,4-diones
with
1,3,5-triazinanes.
In
the
presence
diphosphine
ligand,
proceeds
via
(5+2)
pathway
to
afford
1,3-diazepin-4-ones
in
excellent
yields,
while
using
monophosphine
smoothly
(3+2)
give
imidazolidin-4-ones
good
yields.
Chemical Communications,
Год журнала:
2023,
Номер
59(9), С. 1233 - 1236
Опубликована: Янв. 1, 2023
Herein,
a
palladium-catalyzed
general
synthetic
strategy
to
access
an
attractive
and
decorated
set
of
chiral
spiro
derivatives
benzoxazine
compounds
is
unveiled
utilizing
vinyl
benzoxazinanones
reacted
with
pyrazolone
4,5-diones,
which
extends
the
application
ketones.
This
asymmetric
catalytic
[4+2]
cycloaddition
reaction
demonstrates
broad
substrate
scope
functional
group
tolerance
in
yields
up
76%
96%
ee.
A
facile
scale-up
straightforward
conversion
diversely
substituted
products
verify
utility
this
method.
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(4), С. 1034 - 1041
Опубликована: Янв. 1, 2023
A
series
of
dihydroquinolinones
have
been
synthesized
via
synergistic
catalysis
combining
photolysis
and
Lewis
base
utilizing
in
situ
generated
ketenes
ortho
-amino
MBH
carbonates.
Chinese Journal of Organic Chemistry,
Год журнала:
2022,
Номер
42(10), С. 3051 - 3051
Опубликована: Янв. 1, 2022
Chiral
heterocyclic
compounds
are
an
important
class
of
chiral
substances,
which
widespread
in
many
drugs,
pesticides
and
catalysts.Therefore,
the
efficient
asymmetric
synthesis
these
becomes
a
research
hotspot
organic
synthesis.Transition
metal-catalyzed
cyclization
with
heteroatom-dipole
precursors
is
method
to
construct
frameworks.Among
them,
designed
based
on
transition
allyl
or
propargyl
substitutions
have
been
extensively
studied
past
two
decades
occupied
role
this
field.The
cyclizations
introduced
detail.The
advantages
existing
problems
current
methods
analyzed,
would
provide
useful
reference
for
researchers
related
fields.
Organic Letters,
Год журнала:
2023,
Номер
25(25), С. 4621 - 4626
Опубликована: Июнь 15, 2023
We
present
here
an
iridium-catalyzed
diastereo-
and
enantioselective
[4
+
1]
cycloaddition
reaction
of
hydroxyallyl
anilines
with
sulfoxonium
ylides
under
mild
conditions,
leading
to
3-vinyl
indolines
in
moderate
good
yields
excellent
enantioselectivities.
Control
experiments
disclosed
a
plausible
mechanism.
