Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(37)
Published: June 24, 2023
Abstract
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(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(31)
Published: April 25, 2023
Axially
chiral
compounds
have
been
always
considered
a
laboratory
curiosity
with
rare
prospects
of
being
applied
in
asymmetric
synthesis.
Things
changed
very
quickly
the
last
twenty
years
when
it
was
understood
important
role
and
enormous
impact
that
these
medicinal,
biological
material
chemistry.
The
synthesis
atropisomers
became
rapidly
expanding
field
recent
reports
on
development
N-N
strongly
prove
how
this
research
is
hot
topic
open
to
new
challenges
frontiers
This
review
focuses
advances
enantioselective
highlighting
strategies
breakthroughs
obtain
novel
stimulating
atropisomeric
framework.
Acta Chimica Sinica,
Journal Year:
2023,
Volume and Issue:
81(7), P. 793 - 793
Published: Jan. 1, 2023
o-Hydroxyphenyl
substituted
p-quinone
methides
(p-QMs)
belong
to
a
class
of
p-QMs
with
unique
advantages.They
not
only
maintain
the
high
reactivity
p-QMs,
but
also
have
more
reactive
and
activation
sites
owing
introduction
hydroxyl
group.Therefore,
o-hydroxyphenyl
wide
applications
in
synthetic
medicinal
chemistry.The
catalytic
asymmetric
1,6-conjugate
addition
[4＋n]
cycloaddition
developed
very
rapidly
recent
years,
which
become
efficient
strategies
for
synthesis
chiral
oxygen-containing
heterocycles
arylmethanes
potential
bioactivity.This
review
summarizes
reactions
involving
points
out
remaining
challenges
this
research
area,
will
open
new
window
design
type
their
involved
reactions.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(12), P. 1926 - 1933
Published: May 17, 2023
Abstract
Conjugate
addition
is
one
of
the
most
powerful
and
practical
methods
for
formation
carbon‐carbon
carbon‐heteroatom
bonds
in
organic
synthesis.
Owing
to
rapid
development
asymmetric
catalysis,
significant
progress
has
been
made
field
conjugate
addition,
such
as
1,4‐addition
1,6‐addition.
However,
formidable
challenge
controlling
chemo‐,
regio‐
stereoselectivity
arises
with
extended
conjugated
systems.
Recently,
aid
Brønsted
acids
functionalized
benzyl
alcohols
indolylmethanols
successfully
developed
suitable
precursors
electron‐deficient
systems
organocatalytic
remote
stereocontrolled
additions.
This
review
investigates
advances
enantioselective
1,8‐conjugate
1,10‐conjugate
situ
formed
from
alcohols,
which
organized
according
substrates.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(20), P. 14587 - 14600
Published: Oct. 11, 2023
A
Yb(OTf)3-catalyzed
formal
(4
+
3)
cycloaddition
reaction
of
donor-acceptor
cyclopropanes
with
3-benzylideneindoline-2-thiones
as
sulfur-containing
4π
components
has
been
successfully
achieved.
series
functionalized
5,10-dihydro-2H-thiepino[2,3-b]indole
derivatives
were
synthesized
good
yields
and
moderate
to
diastereoselectivity.
The
described
herein
represented
the
inaugural
3-benzylideneindoline-2-thiones.
Synthesis,
Journal Year:
2023,
Volume and Issue:
56(12), P. 1862 - 1872
Published: Dec. 14, 2023
Abstract
The
construction
of
axially
chiral
alkene
frameworks
is
currently
one
hottest
topics
in
the
field
organic
synthetic
chemistry.
Compared
to
traditional
molecules,
such
as
biaryls,
heterobiaryls,
and
anilides,
synthesis
alkenes
far
more
challenging,
especially
for
acyclic
tetrasubstituted
analogues.
In
this
review,
we
summarized
development
strategies
analogues,
including
asymmetric
difunctionalization,
C–H
functionalization,
cross-coupling,
(dynamic)
kinetic
resolution,
allylic
substitution-isomerization.
1
Introduction
2
Synthesis
Cyclic
Tetrasubstituted
Axially
Chiral
Alkenes
3
Acyclic
4
Summary
Outlook
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(12), P. 3039 - 3044
Published: Jan. 1, 2023
Diastereo-
and
enantioselective
oxa-Nazarov
cyclization-Michael
addition
of
conjugated
1,2-diketones
was
achieved
by
using
asymmetric
binary-acid
catalysis
with
chiral
phosphoric
acid
FeBr
3
.
Angewandte Chemie,
Journal Year:
2023,
Volume and Issue:
135(31)
Published: April 25, 2023
Abstract
Axially
chiral
compounds
have
been
always
considered
a
laboratory
curiosity
with
rare
prospects
of
being
applied
in
asymmetric
synthesis.
Things
changed
very
quickly
the
last
twenty
years
when
it
was
understood
important
role
and
enormous
impact
that
these
medicinal,
biological
material
chemistry.
The
synthesis
atropisomers
became
rapidly
expanding
field
recent
reports
on
development
N−N
strongly
prove
how
this
research
is
hot
topic
open
to
new
challenges
frontiers
This
review
focuses
advances
enantioselective
highlighting
strategies
breakthroughs
obtain
novel
stimulating
atropisomeric
framework.
