Organic Letters,
Год журнала:
2024,
Номер
26(21), С. 4443 - 4450
Опубликована: Май 21, 2024
Highly
functionalized
organic
molecules
are
in
high
demand,
but
their
preparation
is
challenging.
Copper-catalyzed
transformation
of
alkynyl-
and
allenyl-containing
substrates
has
emerged
as
a
powerful
tool
to
achieve
this
objective.
Herein,
an
efficient
copper-catalyzed
difunctionalization
propargylic
carbonates
through
tandem
nucleophilic
substitution/boroprotonation
been
developed,
affording
the
formation
thiol-,
selenium-,
boron-functionalized
alkenes
with
yield
stereoselectivity.
Two
distinct
catalytic
mechanisms
involving
single
reaction
without
any
requirement
catalyst
change
were
successfully
demonstrated.
Chemical Communications,
Год журнала:
2023,
Номер
59(49), С. 7483 - 7505
Опубликована: Янв. 1, 2023
Copper-catalyzed
decarboxylative
reactions
are
powerful
strategies
for
the
construction
of
widely
available
skeletons
such
as
allenes,
ethynyl-containing
heterocycles,
and
quaternary
carbon
centers.
Angewandte Chemie International Edition,
Год журнала:
2023,
Номер
62(47)
Опубликована: Окт. 16, 2023
Abstract
Catalytic
asymmetric
transformations
by
dearomatization
have
developed
into
a
widely
applicable
synthetic
strategy,
but
heavily
relied
on
the
use
of
arenes
bearing
heteroatom.
In
this
case,
is
facilitated
involvement
p
‐orbital
electron
Different
from
conventional
substrate‐dependent
model,
here
we
demonstrate
that
activation
d
transition‐metal
center
can
serve
as
driving
force
for
dearomatization,
and
applied
to
development
novel
alkynyl
copper
remote
substitution
reaction.
A
newly
modified
PyBox
chiral
ligand
enables
construction
valuable
diarylmethyl
triarylmethyl
skeletons
in
high
enantioselectivities.
An
unexpected
tandem
process
involving
sequential
substitution/cyclization/1,5‐H
shift
leads
formation
enantioenriched
C−N
axis.
gram‐scale
reaction
various
downstream
highlight
robustness
method
potential
products.
Preliminary
mechanistic
studies
reveal
mononuclear
Cu‐catalyzed
process.
Organic Letters,
Год журнала:
2023,
Номер
25(8), С. 1274 - 1279
Опубликована: Фев. 17, 2023
A
copper-catalyzed
diastereo-
and
enantioselective
decarboxylative
[3
+
2]
cyclization
reaction
of
alkyne-substituted
cyclic
carbamates
with
azlactones
has
been
established.
range
optically
pure
γ-butyrolactams
bearing
two
vicinal
tetrasubstituted
carbon
stereocenters
were
obtained
in
high
yields
good
to
excellent
stereoselectivities
(up
99%
yield,
99:1
dr,
ee).
This
is
the
first
example
asymmetric
synthesis
containing
sterically
congested
via
a
pathway.
Organic Letters,
Год журнала:
2023,
Номер
25(51), С. 9213 - 9218
Опубликована: Дек. 15, 2023
Herein
we
employed
ethynylethylene
carbonates
(EECs)
to
achieve
formal
[4
+
1]
and
[3
3]
cycloaddition
with
cyclic
1,3-dicarbonyl
compounds.
On
one
hand,
EECs
styryl
substitution
could
undergo
a
remotely
controlled
enantioselective
reaction.
This
reaction
exhibits
good
chemoselectivity,
regioselectivity,
enantioselectivity.
In
addition,
of
compounds
was
also
achieved,
leading
series
4H-pyrans
impressive
chemoselectivity
Organic Letters,
Год журнала:
2022,
Номер
24(28), С. 5120 - 5125
Опубликована: Июль 12, 2022
A
copper-catalyzed
decarboxylative
cascade
cyclization
of
propargylic
cyclic
carbonates/carbamates
with
pyridinium
1,4-zwitterionic
thiolates
is
developed.
range
fused
polyheterocyclic
compounds
are
obtained
in
moderate
to
good
yields
excellent
diastereoselectivities.
Of
particular
note
that
four
new
bonds
(two
C-C,
one
C-O/N,
C-S)
and
stereocenters
could
be
efficiently
embedded
into
the
tetracyclic
scaffolds
a
single
step.
Organic Letters,
Год журнала:
2022,
Номер
24(41), С. 7671 - 7676
Опубликована: Окт. 13, 2022
Enantioselective
construction
of
vicinal
tetrasubstituted
carbon
stereocenters
is
a
formidable
challenge
in
organic
synthesis.
A
copper-catalyzed
asymmetric
decarboxylative
propargylic
substitution
with
3-amino
oxindoles
as
trisubstituted
nucleophiles
and
cyclic
carbonates
tertiary
electrophiles
was
developed.
range
3-amino-3,3′-disubstituted
bearing
quaternary-tetrasubstituted
were
obtained
high
yields
good
to
excellent
stereoselectivities
(up
98%
yield,
>20:1
dr,
98.5:1.5
er).
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 4, 2024
A
palladium-catalyzed
regioselective
[8
+
3]
cycloaddition
of
tropsulfimides
and
tropones
with
vinylidenecyclopropane-diesters
(VDCP-diesters)
has
been
disclosed
in
this
paper,
affording
decahydro-1
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:
2024,
Номер
60(29), С. 3926 - 3929
Опубликована: Янв. 1, 2024
The
unique
Au-allenylidene
promoted
decarboxylative
intramolecular
α
-attacking
annulation
has
been
disclosed
to
prepare
unsaturated
γ
-lactams/lactones
from
cyclic
ethynylethylene
carbamates/carbonates.
