Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
364(3), С. 565 - 573
Опубликована: Окт. 29, 2021
Abstract
Rh(I)‐catalyzed
decarboxylative
arylation
of
alkynyl
cyclic
carbonates
using
commercially
available
and
low‐toxic
aryl
boronic
acids
has
been
disclosed.
Depending
on
the
nature
carbonates,
methodology
provides
a
straightforward
platform
to
access
either
substituted
2,3‐allenols
or
1,3‐butadiene
derivatives.
Internal
undergo
monoarylation
conveniently
afford
with
high
syn
‐selectivity
for
hydroxy
groups.
Whereas,
terminal
led
formation
diarylated
derivatives
having
cis
‐configuration
two
groups
via
allenyl
rhodium(I)alkoxide
intermediate.
The
compatibility
various
functional
allowed
develop
library
diversely
functionalized
scaffolds
excellent
regioselectivity
in
good
yields.
Late‐stage
transformation
series
natural
products
highlights
wide
applicability
process.
Additionally,
scale‐up
experiments
downstream
transformations
α
‐allenol
into
other
valuable
heterocycles
illustrate
efficacy
protocol.
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 Chemistry Frontiers,
Год журнала:
2024,
Номер
11(14), С. 3946 - 3951
Опубликована: Янв. 1, 2024
A
copper-catalyzed
yne-propargylic
substitution
using
amines
as
nucleophiles
has
been
achieved
for
the
first
time,
affording
a
variety
of
having
diyne
moieties,
which
are
important
pharmacophores
in
many
bioactive
molecules.
The Journal of Organic Chemistry,
Год журнала:
2021,
Номер
86(9), С. 6711 - 6720
Опубликована: Апрель 12, 2021
The
first
CuI-catalyzed
decarboxylative
thiolation
of
terminal
alkyne-substituted
cyclic
carbonates/carbamates
to
access
allenes
has
been
developed.
A
wide
range
hydroxymethyl-
and
aminomethyl-containing
allenyl
thioethers
were
smoothly
obtained
in
good
excellent
yields
under
mild
conditions.
copper-allenylidene
intermediate
among
the
process
is
crucial
reaction.
This
method
opens
up
a
new
channel
thioether
compounds.
Chemical Communications,
Год журнала:
2022,
Номер
58(17), С. 2850 - 2853
Опубликована: Янв. 1, 2022
A
copper-catalyzed
enantioselective
[3
+
3]
cycloaddition
of
propargyl
carbonates
and
pyrazolones
has
been
disclosed.
This
reaction
provided
an
efficient
route
to
synthesize
pyranopyrazoles
containing
a
chiral
quaternary
carbon
stereocenter
in
good
yields
with
excellent
enantioselectivities.
In
addition,
the
hydroxyl
group
products
could
be
conveniently
transformed
into
variety
functional
groups,
such
as
aldehyde,
nitrile,
alkene,
ester
amide
which
further
increased
synthetic
value
this
reaction.
Herein
we
describe
the
first
transition-metal-catalyzed
asymmetric
Cloke-Wilson
rearrangement
through
unprecedented
propargylic
alkenoxylation
reaction
with
enol
as
O-nucleophile.
A
set
of
new
chiral
PPBOX
ligands
was
prepared
to
guarantee
high
enantioselectivity
transformation.
series
polysubstituted
dihydrofuran
skeletons
bearing
an
alkyne
unit
in
good
yield
and
under
very
mild
conditions,
various
downstream
transformations
were
facilely
conducted
access
different
skeletons.
Organic Process Research & Development,
Год журнала:
2020,
Номер
24(6), С. 909 - 915
Опубликована: Май 14, 2020
Nonprecious
metal
catalysis
is
a
highly
active
area
of
research
for
both
industrial
and
academic
laboratories.
New
methods
that
efficiently
generate
useful
functionality
in
cost-effective,
high
yielding,
environmentally
friendly
ways
naturally
garner
attention
from
process
chemists
many
different
industries.
This
series
highlights
summarizes
literature
on
the
general
topic
nonprecious
over
four-month
timeframes
will
focus
major
trends
field
are
interest
pharmaceutical
industry.
The
first
installment
selected
transformations
using
copper,
nickel,
iron
catalysts.
ACS Catalysis,
Год журнала:
2021,
Номер
11(19), С. 11843 - 11848
Опубликована: Сен. 9, 2021
A
copper-catalyzed
asymmetric
decarboxylative
propargylic
alkylation
of
enol
carbonates
has
been
realized,
allowing
for
the
highly
stereoselective
formation
acyclic
vicinal
tri-
and
tetrasubstituted
stereocenters.
With
this
strategy,
a
series
optically
active
quaternary
α-amino
acid
esters
with
an
adjunct
chiral
tertiary
moiety
have
prepared
from
propargyl
azlactone-enol
in
high
yields
good
to
excellent
diastereo-
enantioselectivities.
The
success
reaction
exemplifies
potential
strategy
resolve
unmet
challenges
present
traditional
catalytic
alkylation.
Organic & Biomolecular Chemistry,
Год журнала:
2022,
Номер
20(15), С. 3145 - 3153
Опубликована: Янв. 1, 2022
trans
-2-Aroyl-3-arylethyl-cyclopropanes-1,1-dicarboxylates
upon
treatment
with
SnCl
4
underwent
the
Cloke–Wilson
rearrangement
to
give
3,4,5-trisubstituted
γ-butyrolactones
stereoselectively.
