Phosphine‐Catalyzed Divergent γ,γ‐ and ε,γ‐Umpolung Domino Additions of Bisoxindoles with Allenoates: Construction of Vicinal All‐Carbon Quaternary Stereocenters and Formal Total Synthesis of Dimeric Cyclotryptamine Alkaloids
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 25, 2025
Comprehensive
Summary
Vicinal
all‐carbon
quaternary
stereocenters
are
widely
present
in
natural
products
and
bioactive
molecules.
However,
the
construction
of
such
motif
one
step
from
readily
available
starting
materials
remains
a
significant
challenge.
Herein,
we
report
phosphine‐catalyzed
divergent
γ,γ‐
ε,γ‐umpolung
domino
addition
bisoxindoles
with
allenoates.
This
method
serves
as
practical
tool
for
concise
synthesis
series
bisoxindole
derivatives
bearing
sterically
hindered
vicinal
under
mild
reaction
conditions.
The
applicability
this
novel
was
demonstrated
gram‐scale
three
known
advanced
intermediates
total
syntheses
calycanthine,
chimonanthine
folicanthine.
Язык: Английский
Facile synthesis of 2-vinylindolines via a phosphine-mediated α-umpolung/Wittig olefination/cyclization cascade process
Shu‐Hui Li,
Dan Xu,
Hui Yao
и другие.
Chemical Communications,
Год журнала:
2024,
Номер
60(53), С. 6773 - 6776
Опубликована: Янв. 1, 2024
A
novel
phosphine-mediated
α-umpolung/Wittig
olefination/cyclization
cascade
process
between
o
-aminobenzaldehydes
and
Morita–Baylis–Hillman
(MBH)
carbonates
has
been
ingeniously
developed
for
the
facile
synthesis
of
a
broad
range
2-vinylindolines.
Язык: Английский
Acetoxy allenoates as emerging synthons in annulation/cycloaddition reactions
Chemical Communications,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 1, 2025
The
emergence
of
acetoxy
allenoates
as
versatile
synthons
to
generate
a
plethora
annulation/cycloaddition
products
via
electrophilic
diene–phosphonium/ammonium
intermediates
is
highlighted
in
this
feature
article.
Язык: Английский
Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 23, 2025
Herein,
we
developed
an
efficient
nucleophile-controlled
regiodivergent
domino
reaction
between
enetriones
and
γ-bromocrotonates.
This
method
allowed
for
the
rapid
synthesis
of
a
range
1,3-dienic
esters
tetrasubstituted
pyrans
under
metal-free
conditions.
In
presence
pyridine,
SN2
substitution/Michael
addition/elimination
sequence
formed
in
satisfactory
yields
with
high
E-stereoselectivities.
Alternatively,
addition/cyclization/cyclopropanation/cyclopropane
ring-opening
process
forged
good
help
Et3N.
It
is
interesting
to
note
that
site-selective
reactions
γ-bromocrotonates
at
α-
or
γ-position
were
readily
realized
by
modulating
pyridine
Furthermore,
simple
Et3N
act
as
both
nucleophiles
substitution
Lewis
bases
deprotonation
processes.
Язык: Английский
Pyridine-Catalyzed Chemoselective Four-Component Cascade Reaction of Aromatic Aldehydes, Malononitrile/Cyanoacetates, MBH Carbonates, and Alcohols
Organic Letters,
Год журнала:
2024,
Номер
26(36), С. 7576 - 7583
Опубликована: Сен. 3, 2024
An
efficient
pyridine-catalyzed
chemoselective
four-component
cascade
reaction
of
aromatic
aldehydes,
malononitrile/cyanoacetates,
Morita-Baylis-Hillman
(MBH)
carbonates,
and
alcohols
has
been
established.
This
one-pot
progressed
in
an
unusual
with
solvent
participation
via
a
Knoevenagel
condensation/oxa-Michael
addition/S
Язык: Английский
Selective Preparation of Pyrrolo[2,3‐c]tetrahydroquinolines and Indolo[3,2‐c]tetrahydroquinolines through N‐Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl‐Tethered Oximes with Diaryliodonium Salts
Chang-Rui Nie,
Mei-Mei Pan,
Rong Deng
и другие.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
unknown
Опубликована: Окт. 25, 2024
Abstract
We
describe
a
selective
preparation
of
variety
functionalized
pyrrolo[2,3‐
c
]tetrahydroquinolines
and
indolo[3,2‐
in
40–82%
40–80%
yields
from
alkynyl‐tethered
oximes
with
diaryliodonium
triflates,
respectively.
The
one‐pot
reaction
underwent
N
‐arylation,
intramolecular
[3+2]
cycloaddition,
[1.3]
or
[3,3]‐rearrangement
N−O
bond
total
three
steps.
Experimental
studies
revealed
that
EtOAc
solvent
copper(II)‐catalyst
played
crucial
roles
on
the
formation
these
two
tetrahydroquinoline
scaffolds.
Moreover,
scaffolds
could
be
converted
into
various
building
blocks
by
further
transformations.
Язык: Английский
Phosphine-Catalyzed [4 + 1] Annulation of β’-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16711 - 16720
Опубликована: Окт. 31, 2024
A
phosphine-catalyzed
[4
+
1]
annulation
of
β'-acetoxy
allenoate
with
α-alkylidene
succinimides
is
described.
This
method
demonstrates
the
nucleophilic
dialkylation
and
cyclization
succinimides,
resulting
in
formation
functionalized
spirosuccinimide
derivatives.
The
reaction
exhibits
a
wide
substrate
scope
yields
ranging
from
moderate
to
excellent
under
optimized
conditions.
In
addition,
biological
evaluation
indicates
that
cycloadduct
3u
presents
satisfied
inhibitory
activities
for
three
human
cancer
cell
lines
(HCT116,
A549,
HepG2).
Язык: Английский
Controllable Phosphine-Catalyzed Three-Component Domino Reaction of Activated Alkenes with Morita–Baylis–Hillman (MBH) Carbonates: Divergent Synthesis of Densely Functionalized Cyclopentanes and Diquinanes
Organic Letters,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 7, 2024
An
unexpected
phosphine-catalyzed
controllable
three-component
domino
reaction
involving
[1
+
2
2]
annulation
and
2]/[3
sequential
of
2-arylmethylidene
cyanoacetates/malononitriles
with
Morita-Baylis-Hillman
(MBH)
carbonates
has
been
developed.
A
broad
range
densely
functionalized
cyclopentanes
diquinanes
bearing
five
or
four
consecutive
stereogenic
centers,
including
two
all-carbon
quaternary
stereocenters,
were
smoothly
acquired
in
moderate
to
excellent
yields
under
mild
conditions
from
readily
available
materials.
Moreover,
this
divergent
transformation
enables
the
simultaneous
generation
three
new
C-C
bonds
one
carbocyclic
rings
only
step.
Язык: Английский
Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates
Organic Letters,
Год журнала:
2024,
Номер
26(43), С. 9203 - 9209
Опубликована: Окт. 21, 2024
Controlling
the
selectivity
of
reactions
is
a
significantly
attractive
strategy
in
synthetic
organic
chemistry.
Herein,
an
efficient
base-controlled
chemodivergent
domino
reaction
between
o-aminochalcones
and
γ-bromocrotonates
has
been
developed.
A
series
cis-2,3-disubstituted
indolines
cyclopropane-fused
tetrahydroquinolines
were
obtained
via
two
pathways
with
broad
substrate
scope
moderate
to
excellent
yields
under
transition-metal-free
conditions.
It
noteworthy
that
could
be
used
as
C1
or
C2
synthons
by
modulating
base;
particular,
both
nucleophiles
electrophiles
generate
cyclopropanes
for
first
time.
Язык: Английский