Controllable Phosphine-Catalyzed Three-Component Domino Reaction of Activated Alkenes with Morita–Baylis–Hillman (MBH) Carbonates: Divergent Synthesis of Densely Functionalized Cyclopentanes and Diquinanes
Yi Li,
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Xianfei Hu,
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Boning Li
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Dec. 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.
Language: Английский
Pyridine-Catalyzed Chemoselective Four-Component Cascade Reaction of Aromatic Aldehydes, Malononitrile/Cyanoacetates, MBH Carbonates, and Alcohols
Boning Li,
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Xianfei Hu,
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Hui Yao
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(36), P. 7576 - 7583
Published: Sept. 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
Language: Английский
Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids
Durga Golagani,
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Kota Krishna Prakash,
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Satyam Thapa
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et al.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 1, 2024
A
novel
photoinduced
Fe(OTf)
Language: Английский
Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral-Fused Polycyclic Compounds
Rémi Pereira,
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Pierre Locquet,
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Aurélien Blanc
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 21, 2025
Reported
herein
is
a
route
to
functionalized
chiral
heteroaromatic
polycyclic
compounds
leveraging
two
unfriendly
catalytic
cycles
in
one-pot
sequential
process.
α-Heteroaromatic-γ-butyrolactones
were
engaged
highly
regio-,
diastereo-,
and
enantio-selective
Lewis
base
asymmetric
allylic
alkylation
(AAA)
with
alkyne-functionalized
Morita–Baylis–Hillman
(MBH)
carbonates.
Gratefully,
due
the
low
catalyst
loading,
subsequent
gold-catalyzed
Friedel–Crafts
type
cyclization,
entailing
formation
of
fused
compounds,
proceeded
efficiently,
affording
structurally
complex,
enantioenriched
products.
Language: Английский
Directing Group-Controlled Regioselective [4 + 3] Annulation of Indole-2-Carboxamides with MBH Carbonates toward Highly Substituted Indole-1,2-Fused Diazepanones
Shutao Wang,
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W. Y. Zhang,
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Zhuoqi Zhang
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et al.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 11, 2025
A
Lewis
base-catalyzed
[4
+
3]
annulation
between
dinucleophilic
indole-2-carboxamides
and
Morita-Baylis-Hillmann
(MBH)
carbonates
was
developed
to
access
densely
substituted
indole-1,2-fused
diazepanones.
This
reaction
is
initiated
by
a
N-allylic
alkylation
of
the
indole
scaffold
with
MBH
carbonates,
followed
intramolecular
Michael
cyclization.
Notably,
selectivity
this
process
controlled
removable
o-methoxyphenyl
(OMP)
directing
group
attached
indole-2-carboxamides.
The
wide
scope
substrates,
high
regio-
stereoselectivity,
diverse
transformations
highlight
potential
synthetic
utility
method
in
drug
discovery.
Language: Английский
NHC/Pd Synergistically Catalyzed Direct Aerobic Oxidative Allylic Esterification of Aldehydes
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 21, 2025
N-Heterocyclic
carbene
(NHC)-mediated
aerobic
oxidation
of
aldehydes
has
gained
interest
in
recent
years.
However,
its
application
NHC/Pd
synergistic
catalysis
been
unexplored.
We
have
developed
a
strategy
to
synthesize
allylic
esters
directly
from
and
Morita-Baylis-Hillman
(MBH)
carbonates
using
(cooperative)
under
conditions.
This
transformation
gives
access
the
selective
formation
multifunctionalized
E-alkenes
by
β-attack
on
MBH
carbonates.
catalytic
system
also
allows
use
water
as
cosolvent
air
sole
green
oxidant.
Language: Английский
DABCO-catalyzed mono- and bisallylation of β,γ-unsaturated ketones with Morita-Baylis-Hillman carbonates
Guizhou Yue,
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Biao Du,
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Qiumi Wang
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et al.
New Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
48(35), P. 15446 - 15451
Published: Jan. 1, 2024
Mono-
and
bisallylation
of
β,γ-unsaturated
ketones
with
MBH
carbonates
in
the
presence
DABCO
at
rt,
offered
α-2-alkoxycarbonyl,
α,α-di(2-alkoxycarbonyl)
α,γ-di(2-alkoxycarbonyl)
α,β-unsaturated
moderate
to
excellent
yields.
Language: Английский