Diversity‐Oriented Catalytic Asymmetric Dearomatization of Indoles with o‐Quinone Diimides
Advanced Science,
Год журнала:
2023,
Номер
10(35)
Опубликована: Окт. 23, 2023
Abstract
Herein,
the
first
diversity‐oriented
catalytic
asymmetric
dearomatization
of
indoles
with
o
‐quinone
diimides
(
‐QDIs)
is
reported.
The
(CADA)
one
research
focuses
in
terms
structural
and
biological
importance
dearomatized
indole
derivatives.
Although
great
achievements
have
been
made
target‐oriented
CADA
reactions,
reactions
are
regarded
as
more
challenging
remain
elusive
due
to
lack
synthons
featuring
multiple
reaction
sites
difficulty
precise
control
chemo‐,
regio‐,
enantio‐selectivity.
In
this
work,
‐QDIs
employed
a
versatile
building
block,
enabling
chemo‐divergent
dearomative
arylation
[4
+
2]
cycloaddition
indoles.
Under
catalysis
chiral
phosphoric
acid
mild
conditions,
various
indolenines,
furoindolines/pyrroloindolines,
six‐membered‐ring
fused
indolines
collectively
prepared
good
yields
excellent
enantioselectivities.
This
synthesis
protocol
enriches
chemistry
offers
new
opportunities
for
reactions.
Язык: Английский
Catalytic Asymmetric Dearomative Arylation of 2‐Naphthols Enabled by o‐Quinone Diimides
Yuan‐Yang Li,
Fu‐Yuan Yang,
Meng‐Yuan Wu
и другие.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(20), С. 4238 - 4243
Опубликована: Март 16, 2024
Abstract
The
catalytic
asymmetric
dearomative
arylation
of
2‐naphthols
enabled
by
the
unconventional
reactivity
o
‐quinone
diimides,
i.
e.
1,4‐conjugate
addition
on
quinone
sp
2
hybridized
carbon,
has
been
established.
Under
catalysis
chiral
phosphoric
acid,
various
cyclohexaenones
bearing
an
all‐carbon
quaternary
stereocenter
have
prepared
with
excellent
yields
and
enantioselectivities.
Язык: Английский
Regioselective N-arylation of N-Acylsulfenamides Enabled by o-Quinone Diimides
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 27, 2025
The
functionalization
of
N-acylsulfenamides
is
a
research
focus
in
organosulfur
chemistry,
as
the
N-S
array
has
unique
properties
and
versatile
applications.
Although
great
progress
been
made
S-functionalization,
N-functionalization,
especially
N-arylation
N-acylsulfenamides,
rarely
explored
because
lower
nucleophilicity
N-site.
Herein,
we
report
Brønsted
acid-catalyzed
regioselective
reaction
with
o-quinone
diimides.
Under
mild
metal-free
conditions,
wide
range
N-arylated
have
prepared
good
yields
excellent
regioselectivity.
ease
gram-scale
synthesis
transformations
into
useful
sulfonamides
demonstrates
their
synthetic
practicality.
Язык: Английский
Enantioselective construction of quaternary stereocenters via organocatalytic arylation of isoxazolin-5-ones with o-quinone diimides
Organic Chemistry Frontiers,
Год журнала:
2023,
Номер
10(24), С. 6081 - 6086
Опубликована: Янв. 1, 2023
A
bifunctional
squaramide
catalyzes
the
enantioselective
arylation
of
isoxazolin-5-ones
with
o
-quinone
diimides
(
-QDIs)
to
give
featuring
an
arylated
quaternary
stereocenter
in
high
yields
and
excellent
enantioselectivities.
Язык: Английский
Recent Advances in the Domino Annulation Reaction of Quinone Imines
Molecules,
Год журнала:
2024,
Номер
29(11), С. 2481 - 2481
Опубликована: Май 24, 2024
Quinone
imines
are
important
derivatives
of
quinones
with
a
wide
range
applications
in
organic
synthesis
and
the
pharmaceutical
industry.
The
attack
nucleophilic
reagents
on
quinone
tends
to
lead
aromatization
skeleton,
resulting
both
high
reactivity
unique
imines.
extreme
value
construction
nitrogen-
or
oxygen-containing
heterocycles
has
attracted
widespread
attention,
remarkable
advances
have
been
reported
recently.
This
review
provides
an
overview
application
cyclic
compounds
via
domino
annulation
reaction.
Язык: Английский
Organocatalytic Diastereo‐ and Enantioselective Michael Addition of α‐Aryl Isocyanoacetates to Aurone‐Derived Azadienes
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(31)
Опубликована: Июнь 17, 2024
Abstract
A
highly
diastereo‐
and
enantioselective
organocatalytic
Michael
addition
of
α‐aryl
isocyanoacetates
to
aurone‐derived
azadienes
under
mild
conditions
has
been
developed.
This
efficient
methodology
enables
access
chiral
α,α‐disubstituted
α‐amino
ester
derivatives
with
two
adjacent
stereocenters,
one
them
quaternary,
bearing
a
benzofuran
scaffold
in
their
structure
high
yields
stereocontrol.
Furthermore,
the
reaction
product
can
be
readily
converted
into
an
acid
yield
via
hydrolysis
isocyano
group
without
compromising
enantioselectivity.
Язык: Английский