The Journal of Organic Chemistry,
Год журнала:
2020,
Номер
85(17), С. 11240 - 11249
Опубликована: Авг. 11, 2020
An
organocatalytic
domino
aza/oxa-Michael/1,6-addition
reaction
of
ortho-tosylaminophenyl
or
ortho-hydroxyphenyl-substituted
para-quinone
methides
and
ynals
has
been
developed.
In
the
presence
20
mol
%
morpholine,
this
unprecedented
cascade
occurs
readily
in
good
yield
(up
to
99%),
providing
a
highly
efficient
synthetic
approach
synthetically
valuable
1,4-dihydroquinolines
4H-chromenes.
Organic Chemistry Frontiers,
Год журнала:
2020,
Номер
7(13), С. 1743 - 1778
Опубликована: Янв. 1, 2020
In
this
review,
we
provide
a
comprehensive
overview
of
recent
progress
in
rapidly
growing
field
by
summarizing
the
1,6-conjugate
addition
and
annulation
reactions
p-QMs
with
consideration
their
mechanisms
applications.
European Journal of Organic Chemistry,
Год журнала:
2020,
Номер
2020(18), С. 2650 - 2692
Опубликована: Фев. 28, 2020
para
‐Quinone
methides
(
p
‐QMs)
are
naturally
occurring
molecules
that
have
been
finding
increasing
synthetic
applications
in
the
last
few
years.
The
presence
of
two
electronically
different
exocyclic
conjugate
substituents
their
structure,
carbonyl
and
methylidene,
leads
to
a
pronounced
reactivity
owing
polarization
molecule.
In
this
sense,
those
prone
undergo
attack
nucleophiles
terminal
carbon
double
bond,
behaving
as
vinylogous
electrophiles
generating
1,6‐addition
products.
context,
years
development
catalytic
approaches
for
1,6‐nucleophilic
addition
reactions
involving
‐QMs
has
attracted
considerable
attention.
Considering
extensive
such
found
decades
reactions,
review
we
comprehensively
discuss
historical
field,
starting
with
early
on
natural
product
synthesis,
going
through
seminal
non‐stereoselective
processes
progressing
cutting‐edge
asymmetric‐catalyzed
approaches.
Journal of the American Chemical Society,
Год журнала:
2021,
Номер
143(23), С. 8583 - 8589
Опубликована: Июнь 1, 2021
A
one-pot
rhodium-catalyzed
C–H
functionalization/organocatalyzed
oxa-Michael
addition
cascade
reaction
has
been
developed.
This
methodology
enables
the
stereodivergent
synthesis
of
diverse
2,3-disubstituted
dihydrobenzofurans
with
broad
functional
group
compatibility
in
good
yields
high
levels
stereoselectivity
under
exceptionally
mild
conditions.
The
full
complement
stereoisomers
chiral
and
3,4-disubstituted
isochromans
could
be
accessed
at
will
by
appropriate
permutations
two
catalysts.
current
work
provides
a
rare
example
catalysts
independently
controlling
contiguous
stereogenic
centers
subsequently
via
two-step
single
operation.
Organic Letters,
Год журнала:
2019,
Номер
21(19), С. 8127 - 8131
Опубликована: Сен. 23, 2019
In
contrast
to
the
well-explored
quinone
methides
(QMs)
and
aza-ortho-QMs,
aza-para-QMs
have
been
rarely
studied
in
terms
of
their
asymmetric
transformations.
Herein,
a
highly
efficient
enantioconvergent
1,8-addition
is
described.
Featuring
remarkable
remote
stereocontrol,
this
reaction
provides
expedient
access
chiral
tetrasubstituted
allenes
bearing
an
adjacent
all-carbon
quaternary
stereocenter
with
high
enantioselectivity
diastereoselectivity.
The Chemical Record,
Год журнала:
2021,
Номер
21(12), С. 4150 - 4173
Опубликована: Авг. 9, 2021
In
the
last
few
years,
there
has
been
an
explosive
growth
in
area
of
para-quinone
methide
(p-QM)
chemistry.
This
boom
is
actually
due
to
unique
reactivity
pattern
p-QMs,
and
also
their
remarkable
synthetic
applications.
fact,
p-QMs
serve
as
synthons
for
unsymmetrical
diaryl-
triarylmethanes,
construction
diverse
range
carbocycles
heterocycles.
a
wide
structurally
complex
heterocyclic
frameworks
could
be
accessed
through
transformations
modified
stable
p-QMs.
Therefore,
main
focus
this
review
article
cover
recent
advancements
transition-metal,
Lewis
acid
base-catalyzed/mediated
p-quinone
methides
(p-QMs)
oxygen-
nitrogen-containing
Angewandte Chemie International Edition,
Год журнала:
2021,
Номер
60(27), С. 14921 - 14930
Опубликована: Март 17, 2021
Abstract
A
highly
enantiodivergent
organocatalytic
method
is
disclosed
for
the
synthesis
of
atropisomeric
biaryls
via
kinetic
resolution
inspired
by
a
dipeptide‐phosphonium
salt‐catalyzed
Atherton–Todd
(A‐T)
reaction.
This
flexible
approach
led
to
both
R
‐
and
S
‐enantiomers
fine‐tuning
bifunctional
phosphonium
with
excellent
selectivity
factors
(
s
)
up
1057
525,
respectively.
The
potential
newly
synthesized
O‐phosphorylated
biaryl
diols
was
illustrated
axially
chiral
organophosphorus
compounds.
Mechanistic
investigations
suggest
that
halide
catalyst
differentiates
between
in‐situ‐generated
P‐species
in
A‐T
process,
mainly
involving
phosphoryl
chloride
phosphoric
anhydride,
thus
leading
O‐phosphorylation
reactions.
Furthermore
hydrogen
bonding
interactions
catalysts
phosphorus
molecules
were
crucial
asymmetric
induction.
Chemical Communications,
Год журнала:
2022,
Номер
58(46), С. 6653 - 6656
Опубликована: Янв. 1, 2022
A
Cu-catalyzed
asymmetric
1,6-conjugate
addition
of
in
situ
generated
para-quinone
methides
(p-QMs)
with
β-ketoester
has
been
developed
to
construct
a
ketoester
skeleton
bearing
an
adjacent
tertiary-quaternary
carbon
stereocenter
good
yields
and
high
enantioselectivities.
This
is
the
first
example
metal-catalyzed
transformations
p-QMs,
avoiding
using
pre-synthesized
p-QMs
requiring
bulky
2,6-substitutions
highlighting
new
dual
catalytic
activation
chiral
bis(oxazoline)-metal
complex
acting
as
normal
Lewis
acid
activate
β-ketoesters
source
Brønsted
responsible
for
generating
situ.
Organic Letters,
Год журнала:
2022,
Номер
24(25), С. 4704 - 4709
Опубликована: Июнь 20, 2022
A
novel
visible-light-catalyzed
tandem
radical
addition/1,5-hydrogen
atom
transfer/cyclization
cascade
of
2-alkynylarylethers
with
sulfonyl
chlorides
in
2-methyltetrahydrofuran
was
developed
under
photocatalyst-
and
additive-free
conditions.
This
reaction
relies
on
unique
energy
transfer
solvent-radical
relay
strategies
to
generate
radicals
for
the
preparation
a
series
sulfonyl-functionalized
dihydrobenzofurans
moderate
high
yields
catalyzed
by
visible
light
or
solar
radiation.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(8), С. 2023 - 2036
Опубликована: Фев. 5, 2021
Abstract
Quaternary
phosphonium
salts
have
been
extensively
used
in
organic
synthesis
as
Lewis
acid
organocatalysts.
This
review
covers
recent
applications
of
acidic
catalysts
for
Mannich,
Strecker,
and
Friedel‐Crafts
reactions
the
formation
C−C
bonds,
annulation
reactions,
etc.,
allowing
construction
structurally
diverse
synthetically
useful
architectures.
magnified
image
