Organic Letters,
Journal Year:
2024,
Volume and Issue:
27(1), P. 340 - 345
Published: Dec. 30, 2024
This
work
describes
a
chiral
bifunctional
squaramide/DBU
sequential
catalytic
strategy
for
the
enantioselective
synthesis
of
nonfused
eight-membered
O-heterocycles
through
asymmetric
addition
ynones
to
β,γ-unsaturated
α-ketoesters
followed
by
regio-
and
diastereoselective
cyclization
adduct
intermediates.
Mechanistic
experiments
revealed
that
an
isomerization
process
should
be
involved
in
ring
formation
step,
origin
high
regioselectivity
diastereoselectivity
has
also
been
elucidated
DFT
calculations.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(19), P. 5573 - 5604
Published: Jan. 1, 2024
This
review
has
summarized
the
development
of
organocatalytic
asymmetric
[3
+
3]
cycloadditions
and
given
insights
into
remaining
challenges
to
promote
future
this
field.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: July 23, 2024
Abstract
Catalytic
enantioselective
preparation
of
alkene
atropisomers
with
multiple
stereogenic
elements
and
discovery
their
applications
have
become
significant
but
challenging
issues
in
the
scientific
community
due
to
unique
structures
this
class
atropisomers.
We
herein
report
first
catalytic
atroposelective
cyclopentenyl[
b
]indoles,
a
new
kind
atropisomers,
point
axial
chirality
via
an
unusual
rearrangement
reaction
3‐indolylmethanols
under
asymmetric
organocatalysis.
Notably,
novel
type
promising
developing
chiral
ligands
or
organocatalysts,
discovering
antitumor
drug
candidates
fluorescence
imaging
materials.
Moreover,
theoretical
calculations
elucidated
possible
mechanism
non‐covalent
interactions
control
enantioselectivity.
This
approach
offers
synthetic
strategy
for
elements,
represents
3‐indolylmethanols,
which
will
advance
chemistry
indole
chemistry.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 18, 2025
A
method
for
the
asymmetric
propargylation
and
allenylation
of
isatins
catalyzed
using
chiral
Box-copper/zinc
catalysts
is
described.
By
modulation
metal
solvent,
a
series
3-hydroxy-3-propargyl-2-oxindoles
3-hydroxy-3-allenyl-2-oxindoles
are
selectively
synthesized
in
good
yields
with
excellent
enantio-
regioselectivities.
Chemistry - An Asian Journal,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 25, 2025
Abstract
The
development
of
single
chiral
source‐derived
ligands
to
fine‐switch
enantioselectivity
has
been
a
key
aspect
in
asymmetric
catalysis.
Herein,
this
study,
using
the
same
source
l
‐prolinamide
as
starting
material,
we
synthesize
14
new
diphenyl
ether
bridged
C
2
‐symmetric
rigid
tertiary
amine‐derived
dioxide
(abberviated
BPE‐2NO)
and
9
m
‐phenylene
Phe‐2NO);
their
effectiveness
was
demonstrated
first
switch
palladium(II)‐catalyzed
Friedel–Crafts
alkylation.
In
presence
palladium
acetate
Lewis
acid,
both
enantiomers
indole
derivatives
can
be
prepared
good‐to‐excellent
yields
enantioselectivities
by
Eagle‐shaped
BPE/Phe‐2NO
ligands.
Control
experiments
density
functional
theory
calculations
provide
rational
explanation
for
above
observations.
This
study
alkylation
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(17), P. 4812 - 4819
Published: Jan. 1, 2024
A
catalytic
asymmetric
formal
(2
+
3)
cycloaddition
of
methyl-substituted
2-indolylmethanols
was
established,
which
delivered
various
chiral
pyrroloindoles
in
overall
high
yields
with
excellent
diastereoselectivities
and
good
enantioselectivities.
ChemCatChem,
Journal Year:
2024,
Volume and Issue:
16(21)
Published: July 19, 2024
Abstract
Axially
chiral
furan‐based
scaffolds
have
been
recognized
as
a
class
of
important
five‐membered
heteroaryl
atropisomers,
and
developing
catalytic
atroposelective
reactions
for
constructing
this
is
highly
desirable.
However,
the
construction
such
rather
underdeveloped
due
to
existence
great
challenges
remote
ortho
‐substituents
weak
configurational
stability.
To
overcome
these
challenges,
synthetic
chemists
recently
paid
attention
research
field,
number
axially
constructed
via
using
different
strategies.
This
concept
summarized
advances
in
field
pointed
out
remaining
which
will
promote
further
development
emerging
field.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(17), P. 12559 - 12575
Published: Aug. 27, 2024
The
catalytic
atroposelective
synthesis
of
N–N
axially
chiral
indolylamides
was
established
via
dynamic
kinetic
resolution,
which
makes
use
Lewis
base-catalyzed
asymmetric
acylation
N-acylaminoindoles
as
a
new
type
platform
molecule
with
anhydrides.
By
this
strategy,
series
were
synthesized
in
overall
good
yields
(up
to
98%)
excellent
enantioselectivities
99%
ee).
Moreover,
some
these
display
extent
anticancer
activity,
demonstrates
their
potential
application
medicinal
chemistry.
Therefore,
work
has
not
only
provided
strategy
for
the
monoaryl
indoles
but
also
offered
member
configurational
stability
and
promising
application,
thereby
solving
challenges
indoles.
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(12), P. 9086 - 9091
Published: May 30, 2024
The
Brønsted
acid
catalytic
Csp2–O
amination
of
quinolin-4(1H)-ones
with
3-alkynyl-3-hydroxyisoindolinones
as
animation
reagents
has
been
developed.
cascade
dehydration/conjugate
addition/intramolecular
annulation/ring-opening
reaction
proceeded
smoothly
to
afford
a
broad
scope
aminated
products
high
efficiency.
Furthermore,
the
enantioselective
construction
Csp2–N
atropisomers
was
also
investigated
in
presence
chiral
phosphoric
acid.
Importantly,
this
work
not
only
realized
organocatalytic
but
laid
foundation
for
directly
asymmetric
synthesis
atropisomers.
