Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
63(8)
Published: Dec. 29, 2023
Abstract
In
the
chemistry
community,
catalytic
asymmetric
synthesis
of
furan‐based
compounds
bearing
both
axial
and
central
chirality
has
proven
to
be
a
significant
but
challenging
issue
owing
importance
difficulty
in
constructing
such
frameworks.
this
work,
we
have
realized
first
five‐five‐membered
via
organocatalytic
(2+4)
annulation
achiral
furan‐indoles
with
2,3‐indolyldimethanols
uncommon
regioselectivity.
By
strategy,
furan‐indole
were
synthesized
high
yields
excellent
regio‐,
diastereo‐,
enantioselectivities.
Moreover,
theoretical
calculations
conducted
provide
an
in‐depth
understanding
reaction
pathway,
activation
mode,
origin
selectivity.
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(17)
Published: Jan. 26, 2022
Abstract
The
first
highly
atroposelective
construction
of
N−N
axially
chiral
indole
scaffolds
was
established
via
a
new
strategy
de
novo
ring
formation.
This
makes
use
the
organocatalytic
asymmetric
Paal–Knorr
reaction
well‐designed
N
‐aminoindoles
with
1,4‐diketones,
thus
affording
‐pyrrolylindoles
in
high
yields
and
excellent
atroposelectivities
(up
to
98
%
yield,
96
ee).
In
addition,
this
is
applicable
for
synthesis
bispyrroles
97
More
importantly,
such
heterocycles
can
be
converted
into
organocatalysts
applications
catalysis,
some
molecules
display
potent
anticancer
activity.
work
not
only
provides
but
also
offers
members
atropisomer
family
promising
synthetic
medicinal
chemistry.
ACS Catalysis,
Journal Year:
2021,
Volume and Issue:
11(20), P. 12520 - 12531
Published: Sept. 28, 2021
Axial
chirality
widely
exists
in
natural
products,
pharmaceutical
compounds,
and
other
functional
molecules;
these
axially
chiral
compounds
also
find
wide
utility
as
catalysts
or
ligands
organic
synthetic
chemistry.
Nevertheless,
whereas
significant
progress
has
been
made
toward
the
synthesis
of
enantioenriched
molecules
over
past
two
decades,
strategies
involving
organocatalysis
have
only
started
to
emerge
recently.
N-heterocyclic
carbene
(NHC)
organocatalysts
recognized
be
powerful
tools
for
rapid
construction
complex
molecular
architectures.
However,
previous
works
mainly
focused
on
assembly
point
recently
it
realized
that
asymmetric
axial
could
achieved
by
using
NHCs
organocatalysts.
This
Perspective
highlights
developments
advances
scaffolds
catalyzed
NHCs.
The
aim
this
is
provide
an
overview
area
serve
a
stepping
stone
future
investigations.
Chinese Journal of Chemistry,
Journal Year:
2022,
Volume and Issue:
40(18), P. 2151 - 2160
Published: May 31, 2022
Comprehensive
Summary
A
new
strategy
for
the
enantioselective
synthesis
of
axially
chiral
3,3'‐bisindoles
was
devised
by
direct
coupling
two
indole
rings.
This
makes
use
C3‐umpolung
reactivity
2‐indolylmethanols,
which
enables
catalytic
asymmetric
addition
reaction
2‐indolylmethanols
with
rationally
designed
2‐substituted
indoles,
thus
constructing
3,3'‐bisindole
scaffolds
in
overall
excellent
yields
(up
to
98%)
high
enantioselectivities
96
:
4
er).
approach
not
only
has
overcome
challenges
five‐five‐membered
heterobiaryls,
but
also
represents
a
application
catalysis.
More
importantly,
this
class
can
undergo
variety
post‐functionalizations
give
3,3'‐bisindole‐based
organocatalysts,
have
found
their
preliminary
applications
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(15)
Published: Feb. 7, 2023
This
study
establishes
the
first
organocatalytic
enantioselective
synthesis
of
axially
chiral
N,N'-bisindoles
via
phosphoric
acid-catalyzed
formal
(3+2)
cycloadditions
indole-based
enaminones
as
novel
platform
molecules
with
2,3-diketoesters,
where
de
novo
indole-ring
formation
is
involved.
Using
this
new
strategy,
various
were
synthesized
in
good
yields
and
excellent
enantioselectivities
(up
to
87
%
yield
96
ee).
More
importantly,
class
exhibited
some
degree
cytotoxicity
toward
cancer
cells
was
derived
into
phosphine
ligands
high
catalytic
activity.
provides
a
strategy
for
using
asymmetric
organocatalysis
realize
applications
such
scaffolds
medicinal
chemistry
catalysis.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(37)
Published: June 24, 2023
Catalytic
asymmetric
construction
of
chiral
indole-fused
rings
has
become
an
important
issue
in
the
chemical
community
because
significance
such
scaffolds.
In
this
work,
we
have
accomplished
first
catalytic
(4+2)
and
(4+3)
cycloadditions
2,3-indolyldimethanols
by
using
indoles
2-naphthols
as
suitable
reaction
partners
under
catalysis
phosphoric
acids,
constructing
enantioenriched
six-membered
seven-membered
high
yields
with
excellent
enantioselectivities.
addition,
approach
is
used
to
realize
enantioselective
challenging
tetrahydroindolocarbazole
scaffolds,
which
are
found
show
promising
anticancer
activity.
More
importantly,
theoretical
calculations
pathways
activation
mode
offer
in-depth
understanding
class
indolylmethanols.
This
work
not
only
settles
challenges
realizing
indolyldimethanols
but
also
provides
a
powerful
strategy
for
rings.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(14)
Published: Feb. 10, 2023
Axially
chiral
diaryl
ethers
are
a
type
of
unique
atropisomers
bearing
two
potential
axes,
which
have
applications
in
variety
research
fields.
However,
the
catalytic
enantioselective
synthesis
these
ether
is
largely
underexplored
when
compared
to
asymmetric
biaryl
or
other
types
atropisomers.
Herein,
we
report
highly
efficient
through
an
organocatalyzed
desymmetrization
protocol.
The
phosphoric
acid-catalyzed
electrophilic
aromatic
aminations
symmetrical
1,3-benzenediamine
substrates
afforded
series
excellent
yields
and
enantioselectivities.
facile
construction
heterocycles
by
utilizations
1,2-benzenediamine
moiety
products
provided
access
structurally
diverse
novel
azaarene-containing
