Recent Advances in the Catalytic Asymmetric Friedel–Crafts Reactions of Indoles
ACS Omega,
Год журнала:
2022,
Номер
7(40), С. 35446 - 35485
Опубликована: Окт. 3, 2022
Functionalized
chiral
indole
derivatives
are
privileged
and
versatile
organic
frameworks
encountered
in
numerous
pharmaceutically
active
agents
biologically
natural
products.
The
catalytic
asymmetric
Friedel–Crafts
reaction
of
indoles,
catalyzed
by
metal
complexes
or
organocatalysts,
is
one
the
most
powerful
atom-economical
approaches
to
access
optically
derivatives.
Consequently,
a
wide
range
electrophilic
partners
including
α,β-unsaturated
ketones,
esters,
amides,
imines,
β,γ-unsaturated
α-keto-
α-ketiminoesters,
ketimines,
nitroalkenes,
many
others
have
been
successfully
employed
achieve
plethora
functionalized
moieties.
In
particular,
strategies
for
C–H
functionalization
phenyl
indoles
require
incorporation
directing
blocking
group
azole
ring
indole.
discovery
catalysts
which
can
control
enantiodiscrimination
has
gained
great
deal
attention
recent
years.
This
review
will
provide
an
updated
account
on
application
synthesis
diverse
derivatives,
covering
timeframe
from
2011
today.
Язык: Английский
Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles
Synthesis,
Год журнала:
2023,
Номер
56(03), С. 368 - 388
Опубликована: Окт. 2, 2023
Abstract
This
review
delves
into
recent
advances
and
significant
breakthroughs
in
the
field
of
catalytic
Friedel–Crafts
alkylation
targeted
arenes
or
heteroarenes.
Though
a
few
earlier
literatures
are
referenced,
main
emphasis
this
focuses
on
literature
mainly
published
between
2015
March
2023.
1
Introduction
2
History
Background
3
Alcohols
as
Alkylating
Agents
4
Aldehydes
Ketones
5
Alkyl
Fluorides
6
Epoxides
7
Cyclopropanes
8
Conclusion
Outlook
Язык: Английский
Organocatalyzed Asymmetric Pictet‐Spengler Reactions
ChemistrySelect,
Год журнала:
2023,
Номер
8(3)
Опубликована: Янв. 19, 2023
Abstract
The
Pictet‐Spengler
reaction
is
a
century
old
technique
for
the
construction
of
aza‐cycles,
which
has
been
extensively
researched
through
organocatalytic
methods
over
past
two
decades.
asymmetric
variant
this
gained
considerable
attention
because
enantioenriched
poly
heterocycles
accessed
process
are
prevalent
in
natural
products
and
bioactive
moleculesPrime
focus
review
systematic
chronological
assembly
enantioselective
P−S
catalyzed
by
different
types
organocatalysts.
Mechanistic
approaches
to
rationalize
induction
on
an
additional
flavor
article.
Importance
conventional
justified
synthesis
biologically
naturally
relevant
compounds
have
highlighted
as
well.
Язык: Английский
A concise total synthesis of monoterpenoid indole alkaloid (-)-voacafricine A
Chinese Chemical Letters,
Год журнала:
2025,
Номер
unknown, С. 110913 - 110913
Опубликована: Фев. 1, 2025
Язык: Английский
Remote Stereocontrol in the C6-Functionalization of Indoles via Synergistic Ion-Pair Catalysis
ACS Catalysis,
Год журнала:
2025,
Номер
unknown, С. 9897 - 9908
Опубликована: Май 28, 2025
Язык: Английский
Recent advances in chiral phosphoric acid catalyzed asymmetric organic reactions: An overview
Journal of Molecular Structure,
Год журнала:
2023,
Номер
1297, С. 136919 - 136919
Опубликована: Окт. 28, 2023
Язык: Английский
Enantioselective Pictet–Spengler Reactions
Organic reactions,
Год журнала:
2024,
Номер
unknown, С. 507 - 611
Опубликована: Март 22, 2024
Enantioselective
Pictet–Spengler
reactions
are
promoted
or
catalyzed
by
small
chiral
molecules,
including
Brønsted
acids,
Lewis
and
hydrogen‐bond
donors
(e.g.,
thiourea
compounds).
While
tryptamines
β‐phenethylamines
commonly
used
in
these
reactions,
a
variety
of
other
aryl‐group‐containing
amines
also
viable
substrates.
Achiral
starting
materials
can
participate
cascade
reaction
sequences
that
include
an
enantioselective
step.
Mechanistic
insights
for
transformations
provided
whenever
possible.
The
allows
access
to
heterocyclic
products
otherwise
assembled
via
less
direct
methodologies.
These
employed
as
key
intermediates
the
synthesis
natural
such
yohimbine,
arboricine,
corynantheidine,
mitragynine,
harmicine,
peganumine
A,
deplancheine,
arborescidine
C,
crispine
A.
literature
coverage
this
Chapter
extends
December
2019.
Язык: Английский
C6–H Bond Functionalization of Indoles: A New Gate
Synthesis,
Год журнала:
2023,
Номер
55(21), С. 3417 - 3433
Опубликована: Март 8, 2023
Abstract
Indoles
are
valuable
precursors
in
medicinal,
bioorganic,
and
material
chemistry
particularly
serve
as
a
platform
for
diversity.
However,
the
scope
of
C6-functionalization
indoles
was
limited
until
recently.
In
this
short
review,
we
summarize
developments
reactions
involving
transition-metal-catalyzed
functionalization
Brønsted
Lewis
acid
catalyzed
processes.
The
regioselectivity
is
controlled
by
remote-C–H
activation
hydrogen
bond
formation.
1
Introduction
2
Transition-Metal-Catalyzed
Functionalization
3
Acid-Catalyzed
Processes
4
Conclusion
Язык: Английский
Brønsted acid-catalyzed C6 functionalization of 2,3-disubstituted indoles for construction of cyano-substituted all-carbon quaternary centers
Organic & Biomolecular Chemistry,
Год журнала:
2023,
Номер
21(17), С. 3691 - 3696
Опубликована: Янв. 1, 2023
The
construction
of
cyano-substituted
all-carbon
quaternary
centers
via
Brønsted
acid-catalyzed
direct
C6
functionalization
2,3-disubstituted
indoles
with
2,2-diarylacetonitriles
is
reported.
Язык: Английский
Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums
Chinese Journal of Organic Chemistry,
Год журнала:
2023,
Номер
43(5), С. 1875 - 1875
Опубликована: Янв. 1, 2023
A
nickel-catalyzed
intramolecular
dearomative
arylation
reaction
of
pyridiniums
and
quinoliniums
is
developed.In
the
presence
zinc
powder
as
a
reducing
agent,
Grignard-type
addition
arylbromides
to
C＝N
bonds
proceeds
smoothly
render
pyridines
quinolines
dearomatization,
leading
range
spirooxindole
derivatives
bearing
dihydropyridine
dihydroquinoline
moieties
in
moderate
good
yields.
Язык: Английский