Enantioselective Aminative Dearomatization of Indoles via Electrophilic 1,6-Addition of p-Quinone Diimides (p-QDIs)
Parbat Subba,
Sushree Ranjan Sahoo,
Chhavi Khajuria
и другие.
Organic Letters,
Год журнала:
2024,
Номер
26(23), С. 4932 - 4937
Опубликована: Июнь 3, 2024
Herein
we
report
the
first
use
of
p-quinone
diimide
for
aminative
dearomatization
2,3-disubstituted
indoles
to
furnish
C3
aza-quaternary
chiral
indolenines.
This
approach,
which
proceeds
via
an
electrophilic
1,6-addition
diimide,
allows
synthesis
array
optically
active
indolenines
with
high
yields
and
excellent
enantioselectivities.
A
one-pot
approach
same
has
also
been
established
further
improve
synthetic
accessibility
this
protocol.
Язык: Английский
Organocatalytic Atroposelective Cross-Coupling of 2-Naphthols with Diaryliodonium Salts
Organic Letters,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 17, 2025
Due
to
their
modularity
and
conciseness,
atroposelective
cross-coupling
is
one
of
the
most
attractive
approaches
for
synthesizing
axially
chiral
binaphthyl
molecules.
While
transition
metal-catalyzed
cross-couplings
provide
reliable
synthetic
strategies,
alternative
methods
that
accommodate
a
broader
range
substrates
without
pre-functionalization
are
highly
beneficial.
Here,
we
demonstrate
using
bifunctional
organocatalyst
(DHQD)2PHAL
enables
2-naphthols
diaryliodonium
salts
with
high
efficiency,
yields
(up
72%)
excellent
enantioselectivity
>99%
enantiomeric
excess).
Further
transformations
products
highlight
versatility
other
compounds
while
maintaining
axial
chirality.
Язык: Английский
Dearomative Amination Cyclization of Tryptamines and Tryptophols via Enantioselective 1,6‐Addition of p‐Quinone Diimides (p‐QDIs)
Asian Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 21, 2025
Abstract
A
method
utilizing
p
‐quinone
diimides
(
‐QDIs)
as
electrophilic
nitrogen
source
to
facilitate
a
highly
enantioselective
dearomative
cyclization
of
tryptamine
and
tryptophol
derivatives
has
been
developed.
This
approach
which
proceeds
via
1,6‐addition
‐QDIs
enables
the
rapid
efficient
synthesis
chiral
3‐amino‐pyrroloindoline
3‐amino‐furoindolines
with
excellent
stereochemical
control
(up
99%).
Development
an
alternate
one‐pot
method,
coupled
some
synthetic
transformations
further
elevates
practical
utility
this
strategy.
Язык: Английский
Near-infrared fluorescent indolizine-dicyanomethylene-4H-pyran hybrids for viscosity imaging in living cells
Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy,
Год журнала:
2024,
Номер
316, С. 124330 - 124330
Опубликована: Апрель 23, 2024
Язык: Английский
Asymmetric Cascade Dearomatization–Cyclization Reaction of Tryptamines with β,γ-Alkynyl-α-imino Esters: Access to Hexahydropyrrolo[2,3-b]indole-Containing Tetrasubstituted α-Amino Allenoates
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(14), С. 10148 - 10162
Опубликована: Июль 3, 2024
An
organocatalytic
enantio-
and
diastereoselective
synthesis
of
hexahydropyrrolo[2,3-
Язык: Английский
Chiral Phosphoric Acid-Catalyzed Enantioselective Synthesis of Biphenyl-Bridged ɛ-Sultams via Friedel-Crafts Reactions of Cyclic N-Sulfonylimines with Indolizines
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(17), С. 4829 - 4835
Опубликована: Янв. 1, 2024
An
asymmetric
aza-Friedel–Crafts
arylation
of
biphenyl-bridged
seven-membered
cyclic
N
-sulfonylimines
with
indolizines
via
chiral
phosphoric
acid
is
realized,
affording
indolizine
modified
ε-sultams
up
to
99%
yield
and
ee.
Язык: Английский
Unraveling the Potential of Cyclic N‐Sulfonyl Ketimines in the MCR Universe
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Июль 31, 2024
Abstract
Cyclic
N
‐sulfonyl
ketimines
constitute
an
accessible
class
of
lead‐like
heterocycles
with
a
vast
application
in
both
synthetic
organic
and
medicinal
chemistry.
In
this
context,
we
harness
the
capabilities
these
four
different
isocyanide‐based
multicomponent
reactions.
Our
goal
was
to
create
libraries
compounds
functional
groups
vectors
that
are
compatible
for
structural
elaboration
optimization
their
physical
properties.
We
synthesized
15
unprecedented
high
diversity
complexity,
whereas
have
obtained
single
crystal
structures
each
scaffold,
unraveling
geometrical
features
potential
employment
drug
discovery.
Язык: Английский