Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 17, 2024
Comprehensive
Summary
Terpyridine
ligands
have
been
applied
as
a
class
of
unique
due
to
their
rich
coordination
chemistry
in
the
catalysis.
Herein,
we
developed
new
C
2
‐symmetric
chiral
terpyridine‐pyrroloimidazolone
(TPy‐BPI).
Their
catalytic
activity
was
evaluated
asymmetric
Friedel‐Crafts
alkylation
indoles
with
2,3‐dioxopyrrolidines.
Excellent
yields
(up
92%)
and
high
enantioselectivities
97%
ee)
are
obtained
for
wide
range
substrates
under
mild
conditions.
In
addition
2,3‐dioxopyrrolidines,
β
,
γ
‐unsaturated
α
‐ketoesters
were
also
compatible
Ni(OTf)
‐TPy‐BPI
ligand
L1
‐catalyzed
reaction.
Control
experiments,
single
crystal
structure
two
TPy‐BPI
‐Ni(OTf)
complexes,
DFT
calculations
revealed
origins
enantioselectivity.
To
best
our
knowledge,
work
is
first
report
showing
that
terpyridine
framework
contained
only
nitrogen
atoms
coordinating
metal,
additional
pyridine
unit
acted
stereodirecting
element,
which
different
from
previously
reported
containing
all
three
metal.
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 Chemistry Frontiers,
Год журнала:
2023,
Номер
10(22), С. 5717 - 5734
Опубликована: Янв. 1, 2023
Vinylene
carbonate
(VC)
has
emerged
as
a
promising
coupling
partner
to
participate
in
various
attractive
C–H
conversions
and
implement
an
increasing
number
of
novel
reactions.
In
this
review,
we
provide
summary
the
advancements
achieved
metal-catalyzed
functionalization
using
VC.
Chinese Journal of Chemistry,
Год журнала:
2024,
Номер
42(13), С. 1474 - 1480
Опубликована: Март 1, 2024
Comprehensive
Summary
The
privileged
C
2
‐symmetric
rigid
phenol‐type
ligand
is
more
attractive
but
challenging
in
asymmetric
catalysis.
Herein,
we
designed
and
synthesized
a
class
of
rigid‐featured
chiral
tridentate
Phenol‐2NO
ligands,
that
incorporate
the
advantages
both
phenol
skeleton
pyrroloimidazolone‐based
N
‐oxide
moiety,
from
readily
available
L
‐prolinamides
operationally
simple
two
steps
up
to
44%
overall
yield.
More
importantly,
using
an
achiral
quinoline
derivative
as
additive,
newly
developed
could
serve
anioic
upon
deprotonative
activation
coordinate
Zn(II)
form
highly
enantioselective
catalyst
for
Michael‐type
Friedel‐Crafts
alkylation
reaction
indoles
with
2,3‐dioxopyrrolidines.
Excellent
yields
(up
90%)
high
enantioselectivities
99%
ee)
are
obtained
wide
range
substrates
under
mild
conditions.
Experiments
DFT
calculations
revealed
mechanism
origins
enantioselectivity.
This
also
represented
first
ligand/metal
complex
by
organic
base
additive
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(47)
Опубликована: Окт. 19, 2023
Abstract
The
alkyne
group
is
the
key
component
of
many
bioactive
molecules
and
versatile
synthetic
building
block,
thus
introduction
which
into
target
has
attracted
considerable
interest
from
scientists.
Moreover,
tertiary
quaternary
stereocenters
are
common
motifs
in
natural
products
drugs,
however,
asymmetric
construction
such
one
challenging
tasks
due
to
steric
congestion
multiple
stereospecific
substituents
attached
carbon.
Metal–allenylidene
an
excellent
type
electrophilic
species.
addition
carbon‐nucleophiles
at
Cγ
metal–allenylidene
provides
effective
way
construct
as
well
introduce
group.
In
this
review,
state‐of‐the‐art
propargylic
C−C
bond
formation
via
metal‐allenylidene
generated
situ
alcohol
derivatives
presented.
Synthetic
applications,
mechanistic
insights
addressed.
challenges
opportunities
field
also
discussed.
Abstract
Two
novel
copper-catalyzed
cyclization
reactions
involving
a
remote
propargylic
substitution/cyclization/isomerization
cascade
are
disclosed.
Derivatives
of
the
seldomly
studied
heterocycles
thieno[2,3-c]pyrrole
and
thieno[2,3-d]pyridazine
conveniently
synthesized
in
moderate
to
good
yields
from
primary
amines
or
arylhydrazines
through
[4+1]
[4+2]
reactions,
respectively.
Preliminary
mechanistic
experiments
corroborated
occurrence
designed
reactions.
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.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(8), С. 1671 - 1675
Опубликована: Янв. 1, 2024
The
development
of
efficient
and
straightforward
strategies
for
obtaining
chiral
complex
molecules
from
readily
available
starting
materials
is
great
value
in
drug
discovery.
stereodivergent
synthesis
heterocycles
bearing
quaternary
centers
remains
a
challenge
due
to
inherent
steric
issues.
Herein,
we
report
an
enantioselective
copper-catalyzed
decarboxylative
[3
+
2]
cycloaddition
propargyl
cyclic
carbonates/carbamates
with
4-hydroxycoumarins
afford
wide
range
dihydrofuro[3,2-
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(18), С. 12935 - 12945
Опубликована: Сен. 3, 2024
A
tandem
remote
propargylic
amination/ring
closure/aromatization
reaction
of
vinyl
ethynylethylene
carbonates
and
amines
has
been
developed,
successfully
constructing
pyrrole
derivatives.
The
features
mild
conditions,
high
regioselectivity,
yields,
good
functional
group
tolerance,
making
it
an
efficient
method
for
synthesis.
Importantly,
a
variety
substrates
containing
natural
product
skeletons
could
also
be
compatibly
efficiently
converted
into
pyrroles
under
the
conditions.
