Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(26), P. 5571 - 5576
Published: June 26, 2024
Double
aza-Michael
addition
(DAM)
has
become
an
emerging
strategy
for
the
construction
of
two
carbon–nitrogen
bonds
in
a
single
step,
which
can
significantly
simplify
synthesis
N-heterocycles.
Hitherto,
their
asymmetric
catalytic
genre
remains
unattempted.
Herein,
we
describe
judicious
design
organocatalytic
enantioselective
desymmetric
double
cascade
to
access
series
functionalized
fused
morpholines
with
excellent
yields
and
diastereo-
enantioselectivities.
A
one-pot
telescopic
was
demonstrated
bridged
triheterocyclic
compound.
In
addition,
scale-up
various
attractive
postsynthetic
modifications
title
products
amplify
significance
current
methodology.
Aggregate,
Journal Year:
2023,
Volume and Issue:
4(4)
Published: March 26, 2023
Abstract
The
development
of
rapid,
selective,
and
sensitive
fluorescent
sensors
is
essential
for
visualizing
quantifying
biological
molecules
processes
in
vitro,
ex
vivo,
which
important
not
only
fundamental
studies
but
the
accurate
diagnosis
diseases.
emerging
field
activity‐based
sensing
(ABS),
a
method
that
utilizes
molecular
reactivity
analyte
detection
possesses
many
advantages
including
high
specificity,
sensitivity
accuracy.
aggregation
caused
quenching
phenomenon
occurs
most
conventional
fluorophores
results
reduced
labeling
efficiency
target
analytes
low
photobleaching
resistance,
therefore
limiting
applications
ABS
strategy.
In
contrast,
induced
emission
(AIE)
active
luminogens
(AIEgens)
provide
exceptional
frameworks
ABS.
Of
reaction
classes
utilized
AIEgen
approach,
click
chemistry
has
become
increasing
popular.
this
review,
concepts
approach
with
AIEgens
principles
are
discussed,
followed
by
systematic
summary
application
specific
reactions
protocols
an
array
analytes.
Furthermore,
utility
construction
bioimaging
will
also
be
showcased
throughout
review.
Journal of the American Chemical Society,
Journal Year:
2024,
Volume and Issue:
146(21), P. 14745 - 14753
Published: May 14, 2024
We
herein
describe
a
Ni-catalyzed
formal
hydroamidation
of
readily
available
α,β-unsaturated
carbonyl
compounds
to
afford
valuable
chiral
β-amino
acid
derivatives
(up
>99:1
e.r.)
using
dioxazolones
as
robust
amino
source.
A
wide
range
alkyl-substituted
olefins
conjugated
esters,
amides,
thioesters,
and
ketones
were
successfully
amidated
at
the
β-position
with
excellent
enantioselectivity
for
first
time.
Combined
experimental
computational
mechanistic
studies
supported
our
working
hypothesis
that
this
unconventional
β-amidation
unsaturated
substrates
can
be
attributed
polar-matched
migratory
olefin
insertion
an
(amido)(Cl)Ni
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(10), P. 1622 - 1642
Published: April 8, 2022
Abstract
Aza‐Michael
addition
is
known
to
be
one
of
the
most
exploited
reactions
in
organic
chemistry.
Taking
into
account
fact
that
each
seventh
reaction
pharmaceutical
industry
involves
formation
at
least
C−N
bond,
it
not
surprising
this
especially
valuable
for
synthesis
bioactive
compounds
and
drugs.
Traditionally,
only
push‐pull
alkenes
are
regarded
as
starting
material
reaction.
The
participation
pull‐pull
Michael
acceptors
much
less
studied.
presence
two
vicinal
electron‐withdrawing
groups
makes
them
highly
reactive
nucleophilic
with
nitrogen‐centered
nucleophiles.
This
feature
allows
excellent
building
blocks
molecules
polyfunctional
materials.
review
considers
important
sometimes
unexpected
results
obtained
over
last
decades
on
conjugate
nitrogen
nucleophiles
bearing
various
acceptor
moieties
(alkoxycarbonyl‐,
carbonyl‐,
formyl‐,
cyano‐,
trifluoromethyl‐
or
nitro
group)
combinations.
magnified
image
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(12), P. 1908 - 1925
Published: May 15, 2023
Abstract
The
1,4‐conjugated
addition
of
nitrogen
centered
nucleophiles
to
electron‐deficient
alkenes
is
one
the
most
significant
and
widely
used
reactions
in
modern
synthetic
organic
chemistry.
To
date,
various
protocols
for
aza‐Michael
reaction
have
been
developed.
However,
these
reports
mainly
focus
on
use
strong
Michael
donors.
In
recent
years,
conjugate
weak
acceptors
gained
increasing
popularity.
Impressive
progress
this
area
has
achieved
by
more
efficient
catalyst
systems.
This
review
aims
provide
a
critical
analysis
results
obtained
(azoles,
pyrroles,
indoles,
carbamates,
purines,
amides,
hydrazides,
uraciles
etc
)
with
which
were
reported
over
past
twelve
years.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
11(1), P. 236 - 253
Published: Nov. 30, 2023
In
this
review,
we
elaborate
and
discuss
the
recent
applications
of
straight-chain
amino-α,β-unsaturated
carbonyl
compounds
as
versatile
synthons
in
organocatalytic
reactions
for
creation
five-
six-membered
saturated
nitrogen-containing
heterocycles.
Advanced Science,
Journal Year:
2024,
Volume and Issue:
11(14)
Published: Feb. 7, 2024
Abstract
The
collective
total
syntheses
of
(±)‐hosieines
A–C
with
a
cage‐like
tetracyclic
framework
have
been
realized,
which
includes
the
first
hosieines
B‐C.
key
strategy
synthesis
employs
one‐pot
domino
reaction
that
involves
Cu‐catalyzed
[3+2]
cycloaddition,
1,6‐enone
formation,
and
1,6‐aza‐Michael
addition
forming
5/6/6‐aza‐tricyclic
skeleton.
Other
salient
synthetic
tactics
comprise
challenging
double
bond
migration
1,4‐aza‐Michael
to
afford
framework.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 15, 2025
Herein,
we
disclose
a
novel
organocatalytic
approach
for
the
enantioselective
synthesis
of
1,4-sulfur-bridged
piperidinone
skeletons
via
sequential
aza-Michael/Michael/Mannich
domino
reaction
2-aminochalcones
and
5-alkenyl-thiazolones.
The
one-pot
catalyzed
by
bifunctional
squaramide
catalyst
furnishes
bridged
polycyclic
compounds
with
five
contiguous
stereocenters
(three
tertiary,
two
heteroquaternary)
in
excellent
yields
(up
to
95%)
stereochemical
outcomes
99%
ee
up
>20:1
dr).
methodology
offers
outstanding
control
on
regio-
chemoselectivity,
showcasing
broad
substrate
compatibility.
Additionally,
is
scalable
postsynthetic
transformation
spirothiazolone-tetrahydroquinoline
derivative
further
amplifies
synthetic
utility
methodology.
