Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
134(40)
Published: Aug. 12, 2022
Abstract
Here
we
report
a
new
type
of
chiral
all‐carbon
tetrasubstituted
VQMs
generated
via
phosphoric
acids
catalyzed
nucleophilic
addition
2‐alkynylnaphthols
to
o
‐quinone
methides
or
imines,
which
can
be
captured
intramolecularly
as
result
cycloaddition
reaction.
A
class
naphthyl‐2
H
‐chromenes
bearing
axially
and
centrally
elements
quinone‐naphthols
were
prepared
efficiently
with
good
excellent
yields,
diastereoselectivities
enantioselectivities.
Noteworthy,
the
enantioselective
alkynylnaphthols
proceeded
[2+2]
cycloaddition,
followed
by
retro‐4π‐electrocyclization
6π
re‐cyclization.
While
imines
sequential
[2+4]
an
auto
oxidation
Moreover,
obtained
naphthols
converted
into
valuable
phosphine
ligands
other
functional
molecules.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(40)
Published: Aug. 12, 2022
Here
we
report
a
new
type
of
chiral
all-carbon
tetrasubstituted
VQMs
generated
via
phosphoric
acids
catalyzed
nucleophilic
addition
2-alkynylnaphthols
to
o-quinone
methides
or
imines,
which
can
be
captured
intramolecularly
as
result
cycloaddition
reaction.
A
class
naphthyl-2H-chromenes
bearing
axially
and
centrally
elements
quinone-naphthols
were
prepared
efficiently
with
good
excellent
yields,
diastereoselectivities
enantioselectivities.
Noteworthy,
the
enantioselective
alkynylnaphthols
proceeded
[2+2]
cycloaddition,
followed
by
retro-4π-electrocyclization
6π
re-cyclization.
While
imines
sequential
[2+4]
an
auto
oxidation
Moreover,
obtained
naphthols
converted
into
valuable
phosphine
ligands
other
functional
molecules.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(9), P. 1549 - 1554
Published: March 16, 2022
Abstract
A
metal
and
base‐free,
operationally
simple,
scalable
multicomponent
approach
towards
the
synthesis
of
S
‐diarylmethane
dithiocarbamates
is
reported.
range
structurally
electronically
diverse
p
‐quinone
methides
are
shown
to
react
with
a
variety
amines,
carbon
disulfide
furnish
corresponding
in
good
excellent
yields
under
mild
conditions.
Furthermore,
‐QMs
embedded
aliphatic
substituents
well
accommodated.
Importantly,
these
readily
accessible
compounds
demonstrated
promising
anti‐proliferative
activity
low
micromolar
ranges
lung
adenocarcinoma
cells,
reiterating
importance
developed
methodology.
magnified
image
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(30), P. 4405 - 4422
Published: Jan. 1, 2023
Alkynes
as
unsaturated
hydrocarbons
have
long
been
used
for
cyclization
reactions.
Various
transition
metal-catalyzed
cyclizations
of
alkynes
reported
in
the
past
decades.
In
this
minireview,
we
mainly
summarize
recent
asymmetric
with
other
functional
groups
such
carbonyl-alkynes,
cyano-alkynes,
and
enynes
under
catalytic
system
nickel
chiral
ligands.
Chemical Communications,
Journal Year:
2022,
Volume and Issue:
58(62), P. 8710 - 8713
Published: Jan. 1, 2022
The
unique
reactivity
of
indolyl-substituted
p-QMs
as
a
new
type
two-carbon
synthon
has
been
explored
for
the
first
time
in
novel
iron(III)-catalyzed
tandem
annulation.
This
(2+2)
annulation/retro-4π
electrocyclization/imino-Nazarov
cyclization
cascade
reaction
is
characterized
by
an
unusual
structural
reconstruction
p-QMs,
leading
to
expeditious
assembly
synthetically
important
functionalized
cyclopenta[b]indoles.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(8), P. 1299 - 1304
Published: Feb. 21, 2023
The
unique
reactivity
of
in
situ
generated
propargylic
para-quinone
methides
as
a
new
type
five-carbon
synthon
has
been
discovered
by
novel
bismuth(III)-catalyzed
tandem
annulation
reaction.
This
1,8-addition/cyclization/rearrangement
cyclization
cascade
reaction
is
characterized
unusual
structural
reconstruction
2-vinylphenol,
involving
cleavage
the
C1'═C2'
bond
and
formation
four
bonds.
method
provides
convenient
mild
approach
to
generate
synthetically
important
functionalized
indeno[2,1-c]chromenes.
mechanism
proposed
from
several
control
experiments.
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(21), P. 5608 - 5618
Published: Jan. 1, 2023
A
boron
Lewis
acid
catalyzes
trans-carboacyloxylations
of
ynamides
with
esters
to
afford
fully
substituted
acyclic
enol
esters/carbonates
in
high
yields
and
excellent
stereocontrol.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(2), P. 882 - 886
Published: Jan. 4, 2024
In
this
work,
we
describe
the
unexpected
2-fold
Csp3–Csp3
bond
cleavage
suffered
by
cyclobutanols
in
presence
of
a
catalytic
amount
Pd(OAc)2
and
promoted
bulky
biaryl
JohnPhos
ligand.
Overall,
sequential
strained
an
unstrained
leads
to
formal
[2
+
2]-retrocyclization
products,
namely,
styrene
acetophenone
derivatives.
This
procedure
might
enable
use
as
masked
acetyl
groups,
resisting
harsh
conditions
organic
synthesis.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(8), P. 5423 - 5433
Published: April 1, 2024
Currently,
most
conventional
methods
to
achieve
imidazo[1,5-a]pyridines
have
limitations
for
the
synthesis
of
3-acyl
imidazo[1,5-a]pyridines.
Herein,
a
novel
and
efficient
Cu(I)-catalyzed
three-component
annulation
method
valuable
by
reaction
2-pyridinyl-substituted
p-QMs,
terminal
alkynes,
TsN3
in
presence
O2
under
mild
conditions
successfully
been
developed.
The
investigation
indicated
that
molecular
oxygen
(O2)
TsN3,
respectively,
serving
as
nitrogen
sources,
were
essential
successful
completion
system.
