Synthesis,
Год журнала:
2021,
Номер
54(02), С. 499 - 505
Опубликована: Июль 29, 2021
Abstract
Herein,
we
present
a
palladium-catalyzed
tandem
[4+1]
cycloaddition
of
4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-ones
with
N-tosylhydrazones.
The
reaction
is
accomplished
by
merging
the
in
situ
generated
aza-ortho-quinone
methides
(aza-o-QMs)
nucleophilic
carbenes.
This
method
enables
construction
diverse
indolines
broad
functional
group
compatibility
good
yields
high
levels
diastereoselectivity
under
mild
conditions.
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.
Organic Letters,
Год журнала:
2021,
Номер
23(8), С. 2884 - 2889
Опубликована: Март 26, 2021
We
present
herein
a
highly
diastereo-
and
enantioselective
Pd-catalyzed
[4
+
2]
cycloaddition
of
benzofuran-derived
azadienes
with
vinyl
benzoxazinanones,
which
represents
rare
stereoselective
this
class
fused
as
two-atom
synthon.
The
use
phosphoramidite
ligand
bearing
chiral
secondary
amine
simple
biphenyl
backbone
proved
to
be
the
key
construct
novel
spirocyclic
tetrahydroquinoline
scaffold
containing
three
contiguous
stereocenters
single
diastereomer
in
high
enantioselectivity.
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.
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.
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.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(19), С. 4461 - 4474
Опубликована: Авг. 11, 2021
Abstract
Vinyl
benzoxazinanones
as
versatile
building
blocks
can
undergo
transition‐metal‐catalyzed
decarboxylation
to
enable
various
kinds
of
interesting
transformations
by
[4+n],
C−H
allylation
arenes
and
other
types
annulations.
Herein,
we
reviewed
the
latest
research
progress
in
application
vinyl
benzoxazinones
metal‐catalyzed
decarboxylative
reactions
illustrate
their
synthetic
value.
magnified
image
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.
Organic Letters,
Год журнала:
2022,
Номер
24(16), С. 3102 - 3106
Опубликована: Апрель 20, 2022
Phosphine-catalyzed
enantioselective
formal
(4
+
2)-cycloadditions
of
2-(4H-benzo[d][1,3]oxazin-4-yl)acrylates
with
isocyanates
have
been
developed
for
the
first
time.
The
initial
SN2'
attack
chiral
phosphine
organocatalyst
on
generated
key
phosphine-containing
dipolar
intermediates,
and
subsequent
cycloaddition
furnished
a
broad
scope
3,4-dihydroquinazolin-2-ones
in
60-84%
yields
61-92%
ee.
