European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(45)
Published: Aug. 22, 2024
Abstract
A
Pd‐catalyzed
umpolung
allylation
of
isatin‐derived
azomethine
imines
with
vinyl
cyclopropanes
was
disclosed.
This
protocol
provides
an
efficient
and
atom‐economic
approach
to
access
array
structurally
interesting
allylic
aminooxindole
derivatives
in
good
yields
linear‐selectivities
(up
95
%
yield).
Further
product
derivatization
asymmetric
catalytic
studies
proved
the
practicability
reaction
potential
application.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(11)
Published: Jan. 20, 2024
Abstract
A
practical
and
mild
electrochemical
dehydrogenative
regioselective
cyclization
method
has
been
established
for
the
synthesis
of
4‐pyrrolin‐2‐ones
using
3‐aza‐1,5‐dienes
1,3‐dicarbonyl
compounds
as
substrates.
This
protocol
is
catalyst‐free,
metal‐free,
does
not
require
oxidizing
agents.
It
exhibits
wide
substrate
compatibility
can
be
easily
scaled
up
to
gram
scale.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(15), P. 3213 - 3217
Published: April 4, 2024
With
in-depth
research
on
1,2-difunctionalization,
remote
difunctionalization
has
garnered
widespread
attention
for
achieving
multifunctionality.
Herein,
we
report
a
strategy
under
mild
conditions.
This
exhibited
good
substrate
suitability
and
functional
group
tolerance.
In
addition,
the
significance
of
this
method
is
further
evidenced
by
its
successful
application
in
scaling
up
conducting
additional
transformations
target
compounds.
Mechanistic
studies
showed
that
radical
might
be
involved
process.
European Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
27(19)
Published: Jan. 11, 2024
Abstract
Vinylcyclopropanes
(VCPs)
are
important
building
blocks
with
multifaceted
reactivity.
Catalytic
asymmetric
ring
opening
of
vinylcyclopropanes
is
a
highly
efficient
process
to
access
valuable
chiral
molecules
diverse
functionalities
that
can
be
further
functionalized
for
series
synthetic
purposes.
VCPs
very
well‐known
substrates
cycloaddition
reactions
and
this
chemistry
has
been
widely
explored.
On
the
contrary,
despite
enormous
potential,
development
new
innovative
strategies
catalytic,
somewhat
underdeveloped.
Recently,
several
significant
examples
have
emerged
in
literature
various
both
activated
unactivated
involve
transition
metal
catalysis.
These
developments
relevant
additions
vinylcyclopropane
chemistry.
In
review,
we
aim
summarize
all
catalytic
transformations
reported
till
date
provide
comprehensive
analysis
these
research
outcomes.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(43), P. 29857 - 29864
Published: Oct. 16, 2024
The
asymmetric
functionalization
of
unstrained
C(sp3)–C(sp3)
bonds
could
be
a
powerful
strategy
to
stereoselectively
reconstruct
the
backbone
an
organic
compound,
but
such
reactions
are
rare.
Although
allylic
substitutions
have
been
used
frequently
construct
C–C
by
cleavage
more
reactive
C–X
(X
is
usually
O
atom
ester)
transition
metals,
reverse
process
that
involves
replacement
bond
with
C–heteroatom
rare
and
generally
considered
thermodynamically
unfavorable.
We
show
unstrained,
inert
σ
can
converted
C–N
via
designed
solubility-control
strategy,
which
makes
unfavorable
possible.
amination
occurs
range
amine
nucleophiles
cleaves
multiple
classes
alkyl
in
good
yields
high
enantioselectivity.
A
novel
resolution
also
reported
transforms
racemic
amines
corresponding
optically
active
sequential
conversion
back
bond.
Mechanistic
studies
formation
rate-limiting
step
driven
low
solubility
salt
formed
from
cleaved
group
nonpolar
solvent.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(2), P. 508 - 513
Published: Jan. 5, 2024
The
enantioselective
allylic
alkylation
of
nitro
ketene
aminals
with
racemic
alcohols
was
realized
by
iridium/acid
dual
catalysis.
An
allyl
group
installed
on
the
α-position
in
a
branched-selective
manner
high
efficiency
excellent
enantioselectivities
(93–99%
ee).
protocol
applied
to
late-stage
modification
neonicotinoid
insecticides,
which
directly
furnished
novel
analogue
good
insecticidal
activity
against
Aphis
craccivora
(LC50
=
6.40
mg/L).
On
basis
control
experiment,
an
aza-ene-type
reaction
mechanism
proposed.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(13), P. 3692 - 3699
Published: Jan. 1, 2024
An
Ir-catalyzed
enantioselective
cascade
allylation/cyclization
reaction
of
2-(1-hydroxyallyl)phenols
was
developed,
affording
antifungal
2-amino-4
H
-chromene
derivatives
with
good
to
excellent
enantioselectivities.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(19), P. 5564 - 5572
Published: Jan. 1, 2024
This
study
reports
the
electrochemical
reaction
of
vinylcyclopropanes
with
sulfonyl
chlorides,
resulting
in
1,5-hydrosulfonylation
and
1,5-chlorosulfonylation.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(20), P. 5831 - 5840
Published: Jan. 1, 2024
An
Ir/Brønsted
acid
dual-catalyzed
asymmetric
cascade
reaction
of
2-(1-hydroxyallyl)phenols
with
isochroman
ketals
was
developed,
affording
antifungal
spiroketals
high
enantioselectivities.
In
the
present
study,
mechanism,
origin
of
chemoselectivity,
and
substituent
effects
phosphine-catalyzed
ring-opening
reaction
cyclopropyl
ketone
have
been
investigated
using
DFT
method.
Multiple
pathways,
including
formation
hydrofluorenone,
Cloke-Wilson
product,
cyclopenta-fused
were
studied
compared.
The
computational
results
show
that
pathway
for
hydrofluorenone
is
most
favorable
one,
which
involves
four
processes:
nucleophilic
substitution
to
open
three-membered
ring,
an
intramolecular
Michael
addition
enolate
intermediate,
[1,5]-proton
transfer
give
ylide,
Wittig
deliver
final
product.
For
disclosing
structural
analysis
local
reactivity
index
performed.
Moreover,
also
considered
QTAIM
analysis.
current
study
would
provide
useful
insights
understanding
chemoselective
reactions.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(97), P. 14451 - 14454
Published: Jan. 1, 2023
Alkene
planar
chirality
is
introduced
in
the
'privileged'
P-alkene
phosphoramidite
ligand
1.
The
resulting
diastereomeric
ligands
(pR,R)-5
and
(pS,R)-5
form
optically
pure
complexes
of
Rh(I)
Pd(II),
which
catalyze
conjugate
additions
boron
C-nucleophiles
to
enones
allylic
alkylations,
respectively.
In
Rh-catalyzed
reaction,
alkene
exerts
absolute
enantiocontrol
over
potent
BINOL
auxiliary.
