Organic Letters,
Год журнала:
2024,
Номер
27(1), С. 340 - 345
Опубликована: Дек. 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.
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Фев. 20, 2025
Lewis
acid-enabled
reactions
of
donor-acceptor
cyclopropanes
(DACs)
with
indoline-2-thiones
are
reported.
The
reaction
exhibits
tunable
annulation
depending
on
the
acid
and
substituent
at
N1
indoline-2-thiones.
With
AlCl3
as
1-isopropylindoline-2-thiones
reactants,
a
direct
ring
opening
DACs,
followed
by
intramolecular
nucleophilic
addition/dehydration
takes
place
leading
to
formation
dihydro-2H-thiepino[2,3-b]indoles
in
moderate
good
yields.
Using
Yb(OTf)3
promoter
1-unsubstituted
(3
+
2)
cycloaddition
DACs
accompanied
sulfur
rearrangement
give
3-indolyl-4,5-dihydrothiophenes
In
addition,
synthetic
transformation
3-indolyl-4,5-dihydrothiophene
sulfone
indole-based
axially
chiral
scaffolds
further
extends
utility
structural
complexity.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(17), С. 4812 - 4819
Опубликована: Янв. 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.
Synthesis,
Год журнала:
2024,
Номер
56(20), С. 3181 - 3190
Опубликована: Июль 5, 2024
Abstract
The
organocatalytic
asymmetric
benzylation
of
Morita–Baylis–Hillman
(MBH)
carbonates
with
2,4-dinitrotoluene
derivatives
as
nucleophiles
is
described.
developed
reaction
provides
a
straightforward
access
to
functionalized
biological
and
synthetic
relevance.
Highly
products
have
been
chemoselectively
efficiently
obtained
in
good
high
yields
(up
84%)
excellent
stereoselectivity
>20:1
dr,
>99
ee).
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(17), С. 12286 - 12297
Опубликована: Авг. 15, 2024
An
efficient
B(C6F5)3-catalyzed
multicomponent
reaction
of
2,3-diketoesters,
amines,
allenes,
and
nucleophiles
was
reported,
which
afforded
2α-functionalized
pyrroles
in
moderate
to
good
yields.
The
features
low
catalyst
loading,
usage
a
small
amount
solvent,
high
atom
economy,
tunable
installation
diverse
functional
groups
at
2α-position,
water
being
formed
as
the
byproduct.
This
is
first
that
combines
vicinal
tricarbonyl
compounds
with
allenes.
ACS Catalysis,
Год журнала:
2024,
Номер
14(21), С. 16256 - 16265
Опубликована: Окт. 19, 2024
Helical
systems
have
attracted
considerable
interest
across
multiple
scientific
fields
due
to
not
only
their
essential
roles
in
biological
processes
but
also
potential
unveil
chirality-associated
phenomena,
properties,
and
functionalities.
Today,
the
distinctive
topologies
of
helicenes
found
extensive
applications
materials
science,
molecular
recognition,
asymmetric
catalysis
owing
structural
diversity
unique
optical
electronic
characteristics.
Nonetheless,
contrast
advancements
synthesis
optically
pure
point-chiral
axially
chiral
compounds,
catalytic
enantioselective
assembly
helically
molecules
remains
its
nascent
stages.
This
Perspective
delves
into
latest
developments
organocatalytic
emphasizing
both
strengths
limitations
existing
literature,
with
perspectives
on
remaining
challenges
within
field.
It
is
expected
that
this
will
serve
as
a
catalyst
for
innovation,
inspiring
creation
more
efficient
strategies
synthesize
molecules.
Chemical Communications,
Год журнала:
2024,
Номер
60(80), С. 11343 - 11346
Опубликована: Янв. 1, 2024
A
substituent-dependent
synthetic
strategy
to
precisely
convert
easily
accessible
phenylallenyl
phosphine
oxides
into
phenanthren-9-yldiphenylphosphine
and
benzo[
b
][1,4]oxaphosphinin-4-iums
is
reported.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(22), С. 16736 - 16749
Опубликована: Окт. 30, 2024
The
enantioselective
synthesis
of
eight-membered
cyclic
ether
has
always
been
a
challenge
in
organic
synthesis.
Herein,
we
reported
highly
tandem
cyclization
reaction
alkyne
ketone
and
dioxypyridines
mediated
by
chiral
bifunctional
catalysts.
This
generates
two
adjacent
stereocenters
using
an
atomeconomic
manner,
providing
simple
effective
method
for
the
one-step
ethers.
