Chemical Communications,
Год журнала:
2022,
Номер
58(21), С. 3493 - 3496
Опубликована: Янв. 1, 2022
An
efficient
and
concise
strategy
has
been
successfully
developed
for
merging
spiro-tetrahydroquinoline
with
spiro-benzofuranone
into
a
single
new
skeleton
through
asymmetric
catalytic
cascade
reactions
catalyzed
by
quinine-derived
chiral
bifunctional
squaramide
organocatalysts.
In
this
approach,
differently
substituted
derivatives
were
smoothly
obtained
high
yields,
excellent
diastereoselectivities
enantioselectivities
(up
to
99%
yield,
up
>20
:
1
dr,
>99%
ee,
40
examples)
under
mild
reaction
conditions.
Organic Letters,
Год журнала:
2023,
Номер
25(25), С. 4621 - 4626
Опубликована: Июнь 15, 2023
We
present
here
an
iridium-catalyzed
diastereo-
and
enantioselective
[4
+
1]
cycloaddition
reaction
of
hydroxyallyl
anilines
with
sulfoxonium
ylides
under
mild
conditions,
leading
to
3-vinyl
indolines
in
moderate
good
yields
excellent
enantioselectivities.
Control
experiments
disclosed
a
plausible
mechanism.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(15)
Опубликована: Фев. 8, 2023
Abstract
Nitrogen‐containing
heterocyclic
compounds
have
consistently
been
a
noticeable
center
of
attention
due
to
their
significant
utilization
in
the
domain
synthetic
organic
chemistry,
agrochemicals,
and
pharmaceuticals.
α,β‐Unsaturated
imines
or
conjugated
provide
lot
cyclic
as
well
acyclic
products
through
reacting
with
versatile
family
compounds.
This
review
summarizes
recent
advances
enantioselective
reactions
α,β‐unsaturated
by
using
methodologies
for
synthesizing
various
nitrogen‐containing
heterocycles
that
contain
four
six‐membered
rings.
The
synthesis
rarely
found
seven‐,
eight‐
nine‐membered
also
reported.
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 Science,
Год журнала:
2021,
Номер
13(3), С. 775 - 780
Опубликована: Дек. 20, 2021
An
unprecedented
redox-neutral
annulation
reaction
of
tertiary
anilines
with
electron-deficient
alkynes
was
developed
that
proceeds
through
a
cascade
Friedel-Crafts
alkylation/[1,5]-hydride
transfer/Mannich
cyclization
sequence.
Under
B(C6F5)3
catalysis,
range
functionalized
1,2,3,4-tetrahydroquinolines
were
facilely
constructed
in
moderate
to
good
yields
exclusive
3,4-anti-stereochemistry.
The
commercial
availability
the
catalyst
and
high
atom
step
economy
procedure,
together
metal-free
external
oxidant-free
conditions,
make
this
an
attractive
method
organic
synthesis.
Organic Letters,
Год журнала:
2022,
Номер
24(20), С. 3747 - 3752
Опубликована: Май 13, 2022
A
phosphine-catalyzed
(4
+
2)
annulation
of
tetrahydrobenzofuranone-derived
allenoates
and
benzofuran-derived
azadienes
(BDAs)
has
been
achieved
to
construct
the
decahydro-2H-naphtho[1,8-bc]furan
derivatives,
which
were
subsequently
treated
with
4-methylbenzenethiol
trimethylamine
produce
thio-Michael
addition
products
in
high
excellent
yields
good
diastereoselectivities.
Organic Letters,
Год журнала:
2022,
Номер
24(16), С. 3102 - 3106
Опубликована: Апрель 20, 2022
Phosphine-catalyzed
enantioselective
formal
(4
+
2)-cycloadditions
of
2-(4H-benzo[d][1,3]oxazin-4-yl)acrylates
with
isocyanates
have
been
developed
for
the
first
time.
The
initial
SN2'
attack
chiral
phosphine
organocatalyst
on
generated
key
phosphine-containing
dipolar
intermediates,
and
subsequent
cycloaddition
furnished
a
broad
scope
3,4-dihydroquinazolin-2-ones
in
60-84%
yields
61-92%
ee.
Chemical Science,
Год журнала:
2023,
Номер
14(18), С. 4893 - 4900
Опубликована: Янв. 1, 2023
An
enantio-
and
diastereoselective
Pd-catalysed
(3
+
2)
cycloaddition
of
bis(trifluoroethyl)
2-vinyl-cyclopropane-1,1-dicarboxylate
(VCP)
with
cyclic
sulfamidate
imine-derived
1-azadienes
(SDAs)
has
been
developed.
These
reactions
provide
highly
functionalized
spiroheterocycles
having
three
contiguous
stereocentres,
including
a
tetrasubstituted
carbon
bearing
an
oxygen
functionality.
The
two
geminal
trifluoroethyl
ester
moieties
can
be
manipulated
in
facially
selective
manner
to
afford
more
diversely
decorated
spirocycles
four
stereocentres.
In
addition,
reduction
the
imine
moiety
also
fourth
stereocentre
exposes
important
1,2-amino
alcohol
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 3413 - 3418
Опубликована: Фев. 20, 2024
An
efficient
cascade
intramolecular
cyclization/intermolecular
nucleophilic
addition
reaction
of
allenyl
benzoxazinone
with
isatin
or
isatin-derived
ketimine
has
been
established
by
using
Pd0-π-Lewis
base
catalysis.
A
series
3-hydroxy-2-oxindoles
and
3-amino-2-oxindoles
quaternary
carbon
atoms
at
the
C3
position
were
synthesized
in
good
yields
under
mild
conditions
through
this
protocol.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(5), С. 3279 - 3291
Опубликована: Фев. 20, 2024
The
construction
of
3,4-dihydroquinolone
derivatives
has
attracted
a
considerable
amount
attention
due
to
their
extensive
applications
in
medicinal
chemistry.
In
this
study,
we
present
the
Pd-catalyzed
[4+2]
cycloaddition
vinyl
benzoxazinanones
with
α-alkylidene
succinimides
for
efficient
synthesis
3,4-dihydroquinolones.
This
approach
presents
numerous
advantages,
including
ready
availability
starting
materials,
mild
reaction
conditions
without
use
additional
bases,
and
wide
range
substrates.
particular,
all
desired
products
can
be
easily
afforded
high
yields
(≤99%)
excellent
diastereoselectivities
(>20:1).
practicality
reliability
strategy
were
demonstrated
by
successful
scale-up
subsequent
straightforward
synthetic
transformations.
Herein,
we
have
developed
a
method
for
the
construction
of
spiro[benzofuran-2,2'-bicyclo[2.1.1]hexanes]
via
BF3·Et2O-catalyzed
formal
[2π
+
2σ]
cycloaddition
bicyclo[1.1.0]butanes
with
benzofuran-derived
oxa(aza)dienes.
This
transformation
allowed
facile
access
to
variety
functionalized
spiro-bicyclo[2.1.1]hexanes
in
good
yields
(up
99%
yield)
excellent
regioselectivities
and
broad
substrate
scope
(34
examples)
under
mild
reaction
conditions.
Moreover,
synthetic
utility
cycloadducts
were
further
emphasized
through
scale-up
experiment
subsequent
transformations.
