Abstract
A
simple
and
beneficial
strategy
for
the
construction
of
2,3‐dihydrofurans
from
α‐bromochalcones
α‐substituted
cyanoketones
via
Michael
addition‐alkylation
reaction
has
been
realized.
This
transformation
was
well
compatible
with
various
cyanoketones,
corresponding
multifunctionalized
were
obtained
in
up
to
98
%
yield.
highly
diastereoselective
variant
also
developed.
Moreover,
could
be
performed
on
gram‐scale.
Organic & Biomolecular Chemistry,
Год журнала:
2024,
Номер
22(7), С. 1346 - 1359
Опубликована: Янв. 1, 2024
Curcumin
and
its
analogs,
display
Michael
donor–acceptor
ability
with
various
reactants
in
the
presence
of
bases,
Lewis
acids
catalysts,
under
conventional,
microwave
mechanochemical
conditions
generate
diverse
synthetic
scaffolds.
Asian Journal of Organic Chemistry,
Год журнала:
2021,
Номер
10(6), С. 1345 - 1376
Опубликована: Апрель 19, 2021
Abstract
Chiral
analogues
of
squaramides
have
been
fruitful
in
organocatalyzed
asymmetric
reactions
over
last
decade.
Alongside
other
H‐bonding
catalysts
like
ureas,
thioureas:
proved
to
be
efficient
for
the
formation
acyclic
and
cyclic
chiral
molecules.
A
wide
range
molecules
bearing
multiple
functionalities
stereocenters
synthesized
by
using
several
bifunctional
as
catalysts.
These
perform
base
utilizing
basic
N
atom
their
extension
help
stereoinduction
forming
H‐bonds
with
suitable
H‐bond
acceptors.
The
present
review
focuses
on
assembling
recent
progresses
synthesis
five
six
membered
rings
promoted
squaramides.
handful
articles
published
research
groups
documenting
construction
five‐
six‐membered
part
interesting
complex
molecular
architectures.
Different
methodologies
conventional
formal
cycloadditions
or
cascade
engineered
through
assistance
fabricate
carbo‐
heterocycles.
This
also
includes
dual
cooperative
catalytic
system
which
squaramide
is
one
The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(14), С. 8825 - 8843
Опубликована: Июнь 11, 2020
The
reaction
of
β-ketosulfones
with
different
α-functionalized
nitroalkenes
affords
diversely
substituted
sulfonylfurans
and
dihydrofurans.
Furthermore,
react
α-bromonitroalkenes
α-hydrazinonitroalkenes
via
a
cascade
Michael
addition-cyclization
protocol
to
afford
nitrodihydrofurans
hydrazinodihydrofurans,
respectively,
bearing
key
sulfonyl
group,
in
excellent
yields
broad
substrate
scope.
Application
these
products
has
been
demonstrated
by
the
synthesis
pyrroles
pyrazoles
good
yields.
nitroallylic
acetates
tetrasubstituted
furans
through
SN2'-intramolecular
reaction,
followed
aromatization.
gram-scale
representative
example
was
carried
out
demonstrate
synthetic
efficiency
methodology.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(31), С. 6243 - 6262
Опубликована: Янв. 1, 2023
This
article
reviews
the
recent
applications
of
Morita–Baylis–Hillman
and
Rauhut–Currier
adducts
nitroalkenes.
It
also
covers
mechanistic
aspects,
including
key
intermediates
reaction
pathways.
New Journal of Chemistry,
Год журнала:
2022,
Номер
46(33), С. 16047 - 16057
Опубликована: Янв. 1, 2022
One-pot
stereoselective
methods
for
the
synthesis
of
hexahydro-9
H
-benzo[
c
]chromen-9-ones
and
hexahydro-1
,6
-chromeno[6,5-
]chromen-1-ones
have
been
developed.
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(9), С. 1872 - 1877
Опубликована: Янв. 1, 2023
Base
mediated
double
and
triple
Michael
reactions
of
curcumin
with
nitrochromene
lead
to
benzochromene
chromenochromenone
skeletons.
A
partial
kinetic
resolution
takes
place
in
the
presence
cinchonidine-squaramide.
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(15)
Опубликована: Фев. 24, 2023
Abstract
An
enantioselective
desymmetrization
of
curcumins
with
3‐olefinic
oxindoles
involving
a
cascade
double‐Michael
addition
strategy
provides
direct
access
to
spirocyclohexanone‐oxindoles
complete
regio‐
and
diastereoselectivities
excellent
enantioselectivities,
besides
good
yields.
The
products
possess
three
contiguous
chiral
centers
multiple
reactive
functionalities.
observed
selectivities
were
rationalized
by
transitions
state
energy
calculations
at
B3LYP//6‐31g(d)
level
DFT.
Beilstein Journal of Organic Chemistry,
Год журнала:
2024,
Номер
20, С. 2016 - 2023
Опубликована: Авг. 15, 2024
A
cascade
inter-intramolecular
double
Michael
strategy
for
the
synthesis
of
highly
functionalized
cyclohexanones
from
curcumins
and
arylidenemalonates
is
reported.
This
works
in
presence
aqueous
KOH
using
TBAB
as
a
suitable
phase
transfer
catalyst
at
room
temperature.
The
are
formed
major
products
moderate
to
excellent
yields
with
complete
diastereoselectivity
most
cases.
triple
adduct,
tetrahydrochromen-4-one,
also
side
product
few
cases
diastereoselectivity.
Physical Sciences Reviews,
Год журнала:
2022,
Номер
7(4-5), С. 345 - 371
Опубликована: Янв. 4, 2022
Abstract
Organocatalysis
has
occupied
sustainable
position
in
organic
synthesis
as
a
powerful
tool
for
the
of
enantiomeric-rich
compounds
with
multiple
stereogenic
centers.
Among
various
molecules
organocatalysis,
formation
carbon–carbon
is
viewed
challenging
issue
synthesis.
The
asymmetric
aldol
and
Michael
addition
reactions
are
most
significant
methods
C–C
bond
forming
reactions.
These
protocols
deliver
valuable
path
to
access
chiral
molecules,
which
useful
synthetic
hybrids
biologically
potent
candidates
desirable
versatile
pharmaceutical
intermediates.
This
work
highlighted
impact
organocatalytic
abundant
solvent
media.
It
focused
on
crucial
construct
high
enantio-
diastereo-selectivity.
