Angewandte Chemie,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 11, 2024
Abstract
Chiral
2‐azetines
and
allenes
are
highly
valuable
structural
units
in
natural
products
useful
chemicals.
However,
enantioselective
synthesis
of
both
has
been
extremely
challenging.
Herein,
we
present
asymmetric
construction
chiral
(70–98
%
yields
up
to
96
ee)
through
phosphine‐catalyzed
[2+2]
annulation
yne‐enones
with
sulfamate‐derived
cyclic
imines.
These
were
easily
transformed
into
upon
treatment
Et
3
SiH,
BF
⋅
2
O
water
at
rt
for
minutes.
Based
on
the
above
transformations,
a
concise
one‐pot
synthetic
procedure
combining
imines
under
phosphine
catalysis
sequential
reduction/isomerization/ring‐opening
reaction
was
thus
set
up,
providing
axially
tetrasubstituted
satisfactory
enantioselectivities
(56–90
91
ee).
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(10), С. 2905 - 2910
Опубликована: Янв. 1, 2024
A
chiral
bifunctional
Brønsted
base-catalyzed
enantioselective
[3
+
2]
cycloaddition
of
D–A
cyclopropanes
and
azadienes
is
reported.
The
protocol
features
broad
substrate
scope,
mild
reaction
conditions
high
functional
group
tolerance.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(10), С. 7169 - 7174
Опубликована: Апрель 29, 2024
α-succinimide-substituted
allenoates
were
employed
as
phosphine
acceptors
in
phosphine-catalyzed
(4
+
2)
annulation
with
1,1-dicyanoalkenes.
They
served
C4
synthons
the
reaction
under
mild
conditions
and
produced
hexahydroisoindole
derivatives
moderate
to
high
yields
good
excellent
diastereoselectivities.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 20, 2025
The
acid-controlled
single-component
retro-aldol/Michael
addition
cascade
reaction
and
[4
+
2]
cycloaddition
of
benzofuran-derived
azadienes
(BDAs)
are
reported
for
the
first
time.
Under
conditions
trifluoromethanesulfonic
acid
as
catalyst
with
water,
BDAs
initiate
retro-aldol
reaction,
followed
by
a
1,4-Michael
addition,
yielding
(arylmethylene)bis(dibenzofuran)
products
excellent
yields
broad
substrate
applicability.
This
represents
application
in
reaction.
In
contrast,
absence
water
boron
trifluoride
etherate
catalyst,
undergo
constructing
spiro[benzofuran-2,3'-benzofuro[3,2-b]pyridine]
framework
high
diastereoselectivity.
method
features
mild
atom
economy,
provides
new
approach
benzofuran
scaffold
derivatives.
Chemical Communications,
Год журнала:
2024,
Номер
60(54), С. 6897 - 6900
Опубликована: Янв. 1, 2024
The
phosphine-catalyzed
(3+3)
annulation
reaction
of
cinnamaldehyde-derived
Morita-Baylis-Hillman
(MBH)
carbonates
with
1,3-dicarbonyl
compounds
as
dinucleophiles
has
been
developed,
giving
hexahydrochromenone
derivatives
in
high
yields
moderate
to
good
diastereoselectivities.
worked
through
double
conjugate
addition
the
phosphonium
intermediates
generated
from
MBH
carbonates.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
22(2), С. 252 - 268
Опубликована: Ноя. 28, 2023
Eight-membered
heterocycles
are
important
but
their
synthesis
is
usually
challenging.
This
review
summarizes
the
recent
advances
in
[4
+
4]
annulation
of
conjugated
heterodienes
with
1,4-dipolar
species
for
assembling
eight-membered
heterocycles.
Organic Letters,
Год журнала:
2023,
Номер
25(48), С. 8547 - 8552
Опубликована: Ноя. 29, 2023
Phosphine-catalyzed
cascade
isomerization/annulation
has
been
developed
to
realize
a
diastereoselective
synthesis
of
allenes
installed
on
the
hexahydropentalene
skeleton,
which
contains
five
chiral
centers
(and
one
axial
chirality).
This
reaction
tolerated
broad
range
allenoates
and
enynes.
The
allene
products
were
transformed
various
halogen-substituted
fused-ring
compounds.
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(18), С. 13030 - 13041
Опубликована: Авг. 30, 2023
A
novel
highly
regio-
and
diastereoselective
phosphine-catalyzed
[2
+
4]
annulation
of
benzofuran-derived
azadienes
(BDAs)
with
acidic
hydrogen-tethered
allyl
carbonates
has
been
developed
ingeniously.
range
functionalized
spiro[benzofuran-cyclohexane]
derivatives
two
consecutive
stereocenters
were
smoothly
obtained
in
moderate
to
excellent
yields
under
mild
reaction
conditions
from
readily
available
materials.
Moreover,
this
method
is
a
practical
scalable
strategy
that
creates
the
core
structural
motif
fungistatic
drug,
griseofulvin.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(16)
Опубликована: Март 20, 2024
Abstract
Phosphine‐catalyzed
chemodivergent
reactions
of
para
‐quinone
methides
(
p
‐QMs)
affording
a
wide
variety
diarylmethyl
thioether
derivatives
have
been
reported.
In
the
transformation
presented
in
this
work,
P(4‐FC
6
H
4
)
3
catalyzed
direct
1,6‐addition
‐QMs
with
thiols,
whereas
P(4‐MeC
promoted
tandem
addition/self‐aldol
condensation
1,4‐dithiane‐2,5‐diol.
Moreover,
some
obtained
products
were
screened
against
cancer
cell
lines
HepG2,
NB4,
and
K562,
one
was
found
to
inhibit
proliferation
all
tested
types.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
unknown
Опубликована: Ноя. 11, 2024
Chiral
2-azetines
and
allenes
are
highly
valuable
structural
units
in
natural
products
useful
chemicals.
However,
enantioselective
synthesis
of
both
has
been
extremely
challenging.
Herein,
we
present
asymmetric
construction
chiral
(70-98
%
yields
up
to
96
ee)
through
phosphine-catalyzed
[2+2]
annulation
yne-enones
with
sulfamate-derived
cyclic
imines.
These
were
easily
transformed
into
upon
treatment
Et
