Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(31), P. 5911 - 5915
Published: Aug. 2, 2023
An
unprecedented
Csp3-H
imination
reaction
using
arylazo
sulfones
as
the
readily
accessible
and
stable
N
source
is
reported.
The
synthetic
virtues
are
demonstrated
through
mild
conditions,
simple
operation,
good
air
compatibility,
functional
group
tolerance,
well
suitability
for
gram-scale
reaction.
resulting
imines
can
be
further
converted
to
α-amino
acids.
presented
results
shed
light
on
an
unusual
usage
of
will
inspire
novel
experimental
design
by
source.
Molecules,
Journal Year:
2025,
Volume and Issue:
30(3), P. 655 - 655
Published: Feb. 1, 2025
This
review
probes
the
recent
developments
in
stereoselective
reactions
within
area
of
sulfoxonium
ylide
chemistry
since
early
2000s.
An
abundance
research
has
been
applied
to
its
emergence
1960s.
There
a
continued
effort
then
with
work
traditional
areas,
such
as
epoxidation,
aziridination
and
cyclopropanation.
Efforts
have
also
novel
olefination
insertion
reactions,
develop
methodologies
using
organocatalysis
transition
metal
catalysis.
The
growing
interrupted
Johnson–Corey–Chaykovsky
is
described,
whereby
unexpected
cyclopropanation
epoxidation
developed.
In
general,
most
observed
mechanistic
pathway
ylides
formal
cycloaddition:
(2
+
1)
(e.g.,
epoxides,
cyclopropanes,
aziridines),
(3
oxetanes,
azetidines),
(4
indanones,
indolines).
involves
formation
zwitterionic
intermediate
through
nucleophilic
addition
carbanion
an
electrophilic
site.
intramolecular
cyclization
occurs,
constructing
cyclic
product.
Insertion
X–H
bonds
X
=
S,
N
or
P)
are
observed,
protonation
followed
by
X,
form
inserted
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(11), P. 1509 - 1512
Published: Jan. 1, 2023
An
efficient
catalyst-
and
additive-free
facile
access
to
rhodanine
S
-alkyl
dithiocarbamate
derivatives
via
multi-component
reaction
of
amines,
CS
2
α-ester
sulfoxonium
ylides
in
methanol
has
been
described.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(26), P. 5500 - 5505
Published: June 20, 2024
Herein,
we
present
a
photoinduced
diastereoselective
C-3
functionalization
of
electrophilic
β-glycosyl
β-lactams.
The
developed
protocol
is
simple,
mild,
and
scalable
explores
the
use
3-exomethylene
β-lactams
as
reaction
partners
in
Giese
type
reaction.
key
nucleophilic
alkyl
radical
generated
by
electron
transfer
process
EDA
complex
formed
NHPI
Hantzsch
esters.
hydrogen
atom
to
β-lactam
intermediate
enables
synthesis
various
N-phenyl
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(23), P. 4061 - 4068
Published: Nov. 5, 2022
Abstract
A
two‐step
protocol
allowing
the
C−H
amination
of
cyclic
ethers
with
iminoiodinanes,
followed
by
reduction
resulting
intermediate
has
been
developed
for
preparation
amino
alcohols.
The
initial
functionalization
is
accelerated
visible
light,
improving
reactivity
compared
to
thermal
process
performed
in
dark.
effect
different
substituents
on
photochemical
iminoiodinanes
studied
both
experimentally
and
computationally.
Photophysical
measurements
DFT
calculations
were
better
understand
observed
reactivities
corroborate
proposed
mechanistic
proposal.
magnified
image
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(18), P. 4474 - 4487
Published: Jan. 1, 2023
Photogenerated
ketenes
simplify
and
accelerate
the
synthesis
of
diverse
cyclic
architectures
demonstrate
their
promising
applications
in
flow
chemistry.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(47), P. 8511 - 8515
Published: Nov. 17, 2023
A
rare
example
of
visible-light-mediated
diverse
reactivity
N-sulfinylamines
with
different
types
carbene
precursors
has
been
disclosed.
Acylsilanes
and
aryldiazoacetates
have
utilized
as
nucleophilic
electrophilic
into
the
N═S═O
linchpin,
to
achieve
valuable
amides
α-iminoesters,
respectively.
Interestingly,
diazocarbonyls
can
also
participate
in
amidation
reaction
via
situ
generated
ketenes.
This
operationally
simple
modular
method
offers
a
mild,
transition-metal-free,
coupling-reagent-free
protocol
fabricate
structurally
promptly
accessible
technique
where
visible
light
remains
key
promoter.
ACS Catalysis,
Journal Year:
2022,
Volume and Issue:
12(19), P. 12302 - 12309
Published: Sept. 28, 2022
Hydroxylamine
derivatives
are
commonly
used
as
both
nitrogen
and
oxygen
sources
in
the
aminohydroxylation
of
alkenes,
which
is
a
powerful
practical
method
for
rapid
assembly
synthetically
useful
1,2-aminoalcohols.
In
this
work,
we
disclose
an
unprecedented
asymmetric
formal
two
diazo
compounds
with
O-benzyl
hydroxylamines,
involves
N–O
bond
activation,
fragment
modification,
reassembly
cascade
process.
This
reaction
forms
multiple
bonds
one-pot,
including
C═N,
C–O,
C–C
bonds,
providing
potent
complement
using
alkenes
to
that
different
compounds,
leading
chiral
α-alkoxy-β-amino-carboxylate
adjacent
tertiary
centers
generally
good
yields
high
excellent
enantioselectivity.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(23), P. 4026 - 4030
Published: Oct. 21, 2022
Abstract
We
report
a
strategy
for
the
preparation
of
1,3‐dicarbonyl
sulfoxonium
ylides
from
α‐diazoketones
and
ylides.
The
transformation
is
achieved
based
on
blue‐LEDs‐promoted
Wolff
rearrangement
α‐diazoketones,
nucleophilic
nature
A
large
array
products
was
prepared
to
demonstrate
substrate
scope
functional
group
tolerance.
plausible
mechanism
proposed
this
experimental
results.
Furthermore,
synthetic
utility
explored.
magnified
image
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(11), P. 3080 - 3088
Published: Jan. 1, 2024
Herein,
we
describe
a
non-covalent
complex-mediated
epoxidation
strategy
that
can
yield
highly
selective
central
spiro-epoxides
by
irradiation
with
visible
light
without
the
need
for
catalyst
addition.
