Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(15), С. 3183 - 3202
Опубликована: Янв. 1, 2023
2-Acetyl-3,4-dihydropyrans,
assembled
from
acetylene
gas
and
ketones
in
a
one-pot
procedure,
are
ethynylated
with
acetylenes
(KOBut/DMSO,
15
°C,
2
h)
to
give
acetylenic
alcohols,
which
readily
cyclize
(TFA,
rt,
5
min)
7-ethynyl-6,8-dioxabicyclo[3.2.1]octanes
up
92%
yield.
The
ring
closure
of
the
above
alcohols
can
be
performed
without
their
isolation
reaction
mixture.
Thus,
synthesis
realized
just
two
synthetic
operations
simple
available
starting
materials
under
mild
transition-metal-free
conditions.
Chemical Society Reviews,
Год журнала:
2022,
Номер
51(10), С. 4146 - 4174
Опубликована: Янв. 1, 2022
The
advances
on
metal-catalysed
high-order
dipolar
annulations
were
comprehensively
summarized
in
this
review.
To
further
exploit
the
potential
of
unique
annulation
strategy,
a
research
outlook
was
also
proposed.
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.
Green Synthesis and Catalysis,
Год журнала:
2021,
Номер
2(2), С. 228 - 232
Опубликована: Апрель 19, 2021
We
reported
a
synergistic
Pd/Cu
catalyzed
enantioselective
decarboxylative
allylation
of
vinylethylene
carbonates
with
glycine
iminoesters,
which
provides
facile
access
to
non-proteinogenic
diverse
trisubstituted
allylic
amino
acid
derivatives
in
high
yields,
exclusive
regioselectivities
and
excellent
stereoselectivities.
This
reaction
tolerates
wide
range
γ
β-aryl
substituted
either
electron-donating
or
electron-withdrawing
groups.
Significantly,
this
method
was
proven
be
sufficient
the
gram
scale
synthesis
chiral
while
retaining
enantioselectivity
geometric
control.
Organic Letters,
Год журнала:
2021,
Номер
23(21), С. 8559 - 8564
Опубликована: Окт. 26, 2021
We
report
asymmetric
[4
+
3]
annulations
between
isatin-derived
Morita–Baylis–Hillman
carbonates
and
two
types
of
vinyl
synergistically
catalyzed
by
tertiary
amines
transition
metals,
through
chemoselective
assemblies
in
situ
formed
allylic
ylides
metal-containing
1,4-dipoles.
A
range
oxepane
frameworks
are
generally
constructed
moderate
to
good
yields
with
high
stereocontrol.
Moreover,
all
four
diastereomers
for
the
products
bearing
vicinal
stereocenters
accessible
tuning
amine
metal
catalysts.
Chemical Communications,
Год журнала:
2024,
Номер
60(13), С. 1774 - 1777
Опубликована: Янв. 1, 2024
A
novel
approach
for
the
synthesis
of
unsaturated
7-membered
lactones
by
Pd-catalyzed
[5+2]
dipolar
cycloaddition
vinylethylene
carbonates
(VECs)
and
C5-substituted
Meldrum's
acid
derivatives
has
been
developed.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(5), С. 1070 - 1077
Опубликована: Янв. 15, 2024
Abstract
Thanks
to
an
unprecedented
gem
‐dialkyl
substituent
effect,
efficient
synthesis
of
tetrahydro
oxepine
derivatives
is
achieved
by
ring
expansion
vinyl
oxetanes
using
acceptor(−acceptor)
diazo
reagents
under
Cu(II)‐catalysis.
A
large
scope
2‐vinyl
and
either
mono
or
diester
give
access
a
series
functionalized
oxepines.
Synthesis,
Год журнала:
2021,
Номер
54(08), С. 1964 - 1976
Опубликована: Дек. 7, 2021
Abstract
In
recent
years,
functionalized
cyclic
organic
carbonates
have
emerged
as
valuable
building
blocks
for
the
construction
of
interesting
and
useful
molecules
upon
decarboxylation
under
transition-metal
catalysis.
By
employing
suitable
catalytic
systems,
development
chemo-,
regio-,
stereo-
enantioselective
methods
synthesis
compounds
has
advanced
greatly.
On
basis
previous
research
on
this
topic,
short
review
highlights
synthetic
potential
catalysis
over
last
two
years.
1
Introduction
2
Transition-Metal-Catalyzed
Decarboxylation
Vinyl
Cyclic
Carbonates
3
Zwitterionic
Enolate
Chemistry
Based
Transition-Metal
Catalysis
4
Alkynyl
Dioxazolones
5
Conclusions
Perspectives
Chemical Communications,
Год журнала:
2022,
Номер
58(46), С. 6646 - 6649
Опубликована: Янв. 1, 2022
In
this
paper,
a
new
type
of
δ-vinylvalerolactone
was
designed
and
synthesized,
used
as
precursor
in
Pd-catalyzed
[6+3]
cycloaddition
with
azomethine
imines,
leading
to
nine-membered
1,2-dinitrogen-containing
heterocycles
77-98%
yields
>20
:
1
d.r.
These
ring-fused
products
were
further
transformed
into
unusual
tetracyclic
bridged-ring
compounds
without
loss
the
diastereoselectivities.
Chemical Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
An
effective
method
for
the
synthesis
of
dihydropyrans
through
synergistic
palladium
and
chiral
phosphonic
acid
catalysis
was
reported.
This
protocol
proceeded
under
mild
reactions
provided
in
up
to
87%
yield
97%
ee.
Organic Letters,
Год журнала:
2021,
Номер
23(12), С. 4715 - 4720
Опубликована: Июнь 7, 2021
An
asymmetric
[3
+
2]
cycloaddition
of
vinyl
ethylenecarbonates
(VECs)
and
(E)-3-arylvinyl
substituted
benzo[d]
isothiazole
1,1-dioxides
has
been
developed
using
the
Pd
complex
a
bidentate
phosphoramidite
(Me-BIPAM)
as
catalyst,
providing
wide
variety
chiral
multistereogenic
vinyltetrahydrofurans
in
good
yields
with
excellent
diastereo-
enantioselectivities
(up
to
>20:1
dr,
99%
ee).
