Palladium-catalyzed decarboxylative (4 + 3) cycloadditions of bicyclobutanes with 2-alkylidenetrimethylene carbonates for the synthesis of 2-oxabicyclo[4.1.1]octanes
Chemical Science,
Год журнала:
2024,
Номер
15(34), С. 13942 - 13948
Опубликована: Янв. 1, 2024
While
cycloaddition
reactions
of
bicyclobutanes
(BCBs)
have
emerged
as
a
potent
method
for
synthesizing
(hetero-)bicyclo[
Язык: Английский
Enantioselective Pd- and Cu-Catalyzed Hydrofunctionalization of Methylenecyclopropanes via a Distal C–C Bond Cleavage
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 28, 2025
The
enantioselective
ring-opening
reactions
of
methylenecyclopropanes
(MCPs)
involving
C–C
bond
activation
via
oxidative
addition
transition
metals
have
been
rarely
reported.
Here,
we
disclose
a
Pd/Cu-catalyzed
enantio-
and
regioselective
coupling
between
cyclic
imino
esters
MCPs
to
produce
α-allylated
2H-pyrrole
derivatives.
In
this
reaction,
azomethine
ylide
formed
by
chiral
copper
catalyst
with
ketimine
ester
would
serve
as
nucleophile
react
activated
palladium
catalysis.
This
bimetallic
system
exhibited
broad
substrate
scope
high
regio-
enantioselectivities.
Язык: Английский
Palladium-catalyzed [4+4] cycloaddition of 2-pyrones with 2-alkylidenetrimethylene carbonates: access to bridged eight-membered oxygen heterocycles
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(10), С. 2864 - 2869
Опубликована: Янв. 1, 2024
A
novel
palladium-catalyzed
[4
+
4]
cycloaddition
of
2-pyrones
with
2-alkylidenetrimethylene
carbonates
has
been
developed
for
the
synthesis
bridged
eight-membered
oxygen
heterocycles
in
good
yields
and
excellent
stereoselectivities.
Язык: Английский
Synthesis of Indole‐Fused Eight‐Membered Oxa‐Rings via Palladium‐Catalyzed Asymmetric [4+4] Cycloaddition of Indole‐2,3‐Quinodimethanes with 2‐Alkylidenetrimethylene Carbonates
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 16, 2024
Comprehensive
Summary
We
report
a
palladium‐catalyzed
asymmetric
[4+4]
cycloaddition
reaction
between
2‐alkylidenetrimethylene
carbonate
and
electron‐deficient
indole‐2,3‐quinodimethanes
(
IQDMs
).
This
features
exclusive
regioselectivity,
high
yield
(up
to
98%),
excellent
enantioselectivity
95%
ee),
easy
scale‐up
without
any
loss
of
efficiency,
making
it
valuable
for
the
synthesis
indole‐fused
eight‐membered
oxa‐rings.
Язык: Английский
Copper‐Catalyzed Formal [4+2] Cycloaddition of Ethynylethylene Carbonates for the Construction of 3,4‐Dihydro‐2H‐benzo[b][1,4]oxazines
Xinzhe Hu,
Haihui Zhu,
Xiang Li
и другие.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(25)
Опубликована: Апрель 9, 2024
Abstract
A
formal
[4+2]
cycloaddition
reaction
of
ethynylethylene
carbonates
and
2‐aminophenols
has
been
developed
for
the
synthesis
3,4‐dihydro‐2
H
‐benzo[
b
][1,4]oxazines
bearing
quaternary
carbon
atoms.
The
features
mild
conditions,
good
functional
group
compatibility
yields.
Furthermore,
when
using
chiral
PyBox
ligand,
this
strategy
could
also
achieve
asymmetric
][1,4]oxazines.
Application
studies
indicated
that
hydroxymethyl
final
products
was
an
excellent
can
be
further
modified
easily.
Язык: Английский
Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(12), С. 8363 - 8375
Опубликована: Июнь 7, 2024
Palladium-catalyzed
decarboxylation
of
5-methylene-1,3-oxazinan-2-ones
and
5-methylene-1,3-dioxan-2-ones
to
generate
aza-π-allylpalladium
oxa-π-allylpalladium
1,4-dipoles
for
[4
+
2]
cycloaddition
reaction
with
1,3,5-triazinanes
was
developed,
affording
a
wide
range
hexahydropyrimidine
1,3-oxazinane
derivatives
in
good
excellent
yields
(up
99%).
The
acyclic
sulfonamido-substituted
allylic
carbonates
as
1,4-dipole
precursors
also
apply
the
developed
synthesized
strategy,
achieving
synthesis
hexahydropyrimidines.
Moreover,
situ-generated
undergoing
dimeric
4]
were
demonstrated
by
construction
1,5-diazocane
derivatives.
Язык: Английский
Unraveling the Potential of Cyclic N‐Sulfonyl Ketimines in the MCR Universe
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 31, 2024
Abstract
Cyclic
N
‐sulfonyl
ketimines
constitute
an
accessible
class
of
lead‐like
heterocycles
with
a
vast
application
in
both
synthetic
organic
and
medicinal
chemistry.
In
this
context,
we
harness
the
capabilities
these
four
different
isocyanide‐based
multicomponent
reactions.
Our
goal
was
to
create
libraries
compounds
functional
groups
vectors
that
are
compatible
for
structural
elaboration
optimization
their
physical
properties.
We
synthesized
15
unprecedented
high
diversity
complexity,
whereas
have
obtained
single
crystal
structures
each
scaffold,
unraveling
geometrical
features
potential
employment
drug
discovery.
Язык: Английский
Type of Tetrahydronaphthalene-Fused 1,5-Dipoles and Their Application in Polycyclic Compounds Synthesis
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(15), С. 10551 - 10556
Опубликована: Июль 17, 2024
Palladium-catalyzed
dipolar
cycloaddition
reactions
represent
an
efficient
strategy
for
the
construction
of
cyclic
compounds,
with
development
novel
precursors
being
a
key
focus.
In
this
study,
new
type
precursor
was
synthesized
through
assembly
vinylethylene
carbonate
unit
and
tetrahydronaphthalene
skeleton.
This
can
undergo
[3
+
2],
[5
4],
2]
reactions,
leading
to
tetrahydronaphthalene-fused
oxazolidin-2-ones,
1,5-oxazonines,
tetrahydrooxepines.
general,
all
these
exhibited
good
reaction
efficiency
functional
group
tolerance.
Язык: Английский
Ytterbium‐Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero‐Allenes for the Synthesis of Diarylmethanes
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
43(2), С. 199 - 204
Опубликована: Окт. 17, 2024
Comprehensive
Summary
A
tandem
Diels–Alder
reaction/Claisen
rearrangement/decarboxylation
strategy
of
N
‐allenamides
(or
aryloxyallenes)
with
3‐alkoxycarbonyl‐2‐pyrones
has
been
developed
for
the
efficient
synthesis
diarylmethanes
moderate
to
good
yields.
The
reaction
exhibits
functional
group
tolerance
and
can
be
applied
late‐stage
modifications
known
drug
molecules.
Mechanistic
studies
indicate
that
ester
at
3‐position
2‐pyrones
is
essential,
initial
between
proximal
C=C
bond
crucial
success
reaction.
Язык: Английский