Atroposelective Synthesis of 2‐Arylindoles via Chiral Phosphoric Acid‐Catalyzed Direct Amination of Indoles†
Chinese Journal of Chemistry,
Год журнала:
2023,
Номер
42(7), С. 731 - 735
Опубликована: Ноя. 29, 2023
Comprehensive
Summary
Indole‐based
atropisomers
are
a
very
important
class
of
axially
chiral
compounds.
However,
the
atroposelective
synthesis
2‐arylindole
remains
largely
unexplored.
In
this
study,
we
report
successful
atropisomeric
2‐arylindoles
using
direct
amination
indoles
with
p
‐quinonediimines
in
presence
phosphoric
acid
as
catalyst.
Quinonediimine
acts
an
aminating
reagent
through
formal
polarity
inversion
imine.
The
malonate
group
on
2‐aryl
2‐indoles
was
found
to
be
essential
for
high
enantioselectivity
products.
This
could
due
additional
interaction
between
ester
and
catalyst,
well
intramolecular
hydrogen
bonding.
Our
findings
provide
new
strategy
asymmetric
construction
atropisomers.
Язык: Английский
Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles
Chinese Journal of Organic Chemistry,
Год журнала:
2024,
Номер
44(6), С. 1786 - 1786
Опубликована: Янв. 1, 2024
Язык: Английский
Recent Advances in Catalytic Transformations of ortho-Alkynylnaphthols
Tetrahedron,
Год журнала:
2025,
Номер
unknown, С. 134726 - 134726
Опубликована: Май 1, 2025
Язык: Английский
Enantioselective Synthesis of Indole‐Derivated Axially Chiral Frameworks via CpXRh(III)‐Catalyzed Domino Cyclization/C3‐Arylation of 2‐Alkynylanilines with 1‐Diazonaphthoquinones
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(5), С. 1064 - 1069
Опубликована: Янв. 13, 2024
Abstract
We
report
herein
a
chiral
Cp
X
Rh(III)‐catalyzed
domino
cyclization/C
3
‐arylation
process
using
2‐alkynylanilines
and
1‐diazonaphthoquinones
as
viable
substrates,
delivering
indole‐based
derivatives
endowed
with
axial
chirality.
The
method
features
high
enantioselectivity,
broad
substrate
scope,
robust
functional
group
tolerance.
Subsequent
functionalization
of
the
synthesized
scaffolds
underlines
practicality
this
approach
in
design
indole‐derivated
axially
frameworks,
demonstrating
its
substantial
promise
synthetic
medicinal
chemistry
applications.
Язык: Английский
Recent advances in atroposelective synthesis of axially chiral heterobiaryl featuring indole frameworks
Jinding Wei,
Minghong Zhu,
Bo Zhang
и другие.
Tetrahedron,
Год журнала:
2023,
Номер
149, С. 133716 - 133716
Опубликована: Ноя. 3, 2023
Язык: Английский
Enantioselective Construction of Axially Iodobenzocarbazole Derivatives by Stereogenic‐at‐Cobalt(III)‐Complex‐Catalyzed Iodoarylation of Alkynes
European Journal of Organic Chemistry,
Год журнала:
2023,
Номер
26(42)
Опубликована: Сен. 7, 2023
Abstract
A
new
synthetic
approach
to
novel
axially
chiral
iodobenzocarbazole
derivatives
based
on
the
highly
enantioselective
intramolecular
iodoarylation
of
linked
alkyne‐indole
systems
was
developed
by
using
versatile
catalyst,
stereogenic‐at‐cobalt(III)‐complex,
through
an
iodinated
vinylidene
o
‐quinone
methide
(IVQM)
intermediate.
This
protocol
provides
21
examples
in
excellent
yields
with
good
high
enantioselectivities
(up
96
%
yield,
98
ee).
Furthermore,
introduced
iodine
atoms
can
easily
be
converted
into
other
functional
groups.
Язык: Английский
Rhodium-Catalyzed Enantioselective Addition of Heteroarenium Salts Enabled by Nucleophilic Cyclization of 2-Alkynylanilines
Organic Letters,
Год журнала:
2023,
Номер
25(47), С. 8439 - 8444
Опубликована: Ноя. 20, 2023
Transition-metal-catalyzed
cyclative
coupling
of
2-alkynylanilines
provides
a
feasible
routine
for
accessing
functionalized
indoles.
Herein,
rhodium-catalyzed
highly
enantioselective
addition
heteroarenium
salts
is
presented,
which
enabled
by
the
nucleophilic
cyclization
2-alkynylanilines.
It
offers
protocols
to
access
enantioenriched
indoles
tethered
1,2-dihydropyridine
and
1,2-dihydroquinoline
motifs
with
excellent
enantioselectivities.
Язык: Английский
Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides
Chemistry - A European Journal,
Год журнала:
2024,
Номер
30(49)
Опубликована: Июнь 26, 2024
Vinylidene
ortho-quinone
methides
(VQMs)
have
been
proven
to
be
versatile
and
crucial
intermediates
in
the
catalytic
asymmetric
reaction
last
decade,
thus
drawn
considerable
concentrations
on
account
of
practical
application
construction
enantiomerically
pure
functional
organic
molecules.
However,
comparison
well
established
chiral
Brønsted
base-catalyzed
via
VQMs,
acid-catalyzed
is
rarely
studied
there
no
systematic
summary
date.
In
this
review,
we
summarize
recent
advances
VQMs
according
three
types
reactions:
a)
intermolecular
nucleophilic
addition
VQMs;
b)
cycloaddition
c)
intramolecular
cyclization
VQMs.
Finally,
put
forward
remained
challenges
opportunities
for
potential
breakthroughs
area.
Язык: Английский