Abstract
A
novel
and
efficient
method
has
been
established
for
synthesizing
a
variety
of
heterotriarylmethanes
with
good
yields
by
employing
metal-free
self-coupling
reaction
benzofuran
azadienes.
The
involvement
t-BuONa
is
essential
in
this
process.
Remarkably,
technique
boasts
mild
conditions
exceptional
compatibility
various
functional
groups,
rendering
it
versatile
invaluable
asset
the
realm
organic
synthesis.
Journal of the American Chemical Society,
Год журнала:
2025,
Номер
unknown
Опубликована: Янв. 2, 2025
Regiodivergent
asymmetric
synthesis
represents
a
transformative
strategy
for
the
efficient
generation
of
structurally
diverse
chiral
products
from
single
set
starting
materials,
significantly
enriching
their
enantiomeric
composition.
However,
design
radical-mediated
regiodivergent
and
enantioselective
reactions
that
can
accommodate
wide
range
functional
groups
substrates
has
posed
significant
challenges.
The
obstacles
primarily
lie
in
switching
regioselectivity
achieving
high
enantiodiscrimination,
especially
when
dealing
with
high-energy
intermediates.
To
address
these
issues,
we
have
developed
new
catalytic
system
integrates
photoinduced
hydrogen
atom
transfer
(HAT)
copper
catalysis,
involving
fine-tuning
ligands,
additives,
other
reaction
parameters.
facilitates
cross-couplings
between
N-aryl
glycine
ester/amide
derivatives
abundant
hydrocarbon
feedstocks
through
strong
C(sp3)–H
bond
activation.
This
approach
allows
controlled
stereoselective
formation
C(sp3)–C(sp3)
C(sp3)–N
bonds,
yielding
rich
variety
C-
or
N-alkylated
esters
amides
commendable
yields
(up
to
92%
yield),
exclusive
regioselectivities
(typically
>20:1
rr),
enantioselectivities
96%
ee).
Our
methodology
not
only
provides
promising
avenue
incorporation
alkyl
functionalities
onto
specific
sites
biologically
molecules
but
also
offers
practical
while
simultaneously
induction
within
photochemical
reactions.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(16), С. 4391 - 4401
Опубликована: Янв. 1, 2024
The
mechanism
and
origin
of
regio-
diastereoselectivity
in
the
reaction
divergent
[3
+
2]
annulation
aliphatic
aldimines
with
alkenes
by
scandium-catalyzed
β-C(sp
3
)–H
activation
have
been
revealed
detail
using
DFT
calculations.
Organic Chemistry Frontiers,
Год журнала:
2024,
Номер
11(10), С. 2905 - 2910
Опубликована: Янв. 1, 2024
A
chiral
bifunctional
Brønsted
base-catalyzed
enantioselective
[3
+
2]
cycloaddition
of
D–A
cyclopropanes
and
azadienes
is
reported.
The
protocol
features
broad
substrate
scope,
mild
reaction
conditions
high
functional
group
tolerance.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(20), С. 15271 - 15281
Опубликована: Окт. 10, 2024
Chiral
bifunctional
thiourea-catalyzed
Diels-Alder
reaction
between
olefinic
azlactones
and
alkylidene
thiazolone
derivatives
is
reported
here
for
the
first
time.
The
asymmetric
delivers
vicinal
tertiary-quaternary
stereocenters
in
spirocyclohexenone
thiazolones
moderate
to
high
yields
good
stereochemical
outcomes.
protocol
can
be
adapted
a
broad
array
of
substrates.
Moreover,
scaled
up,
chiral
was
converted
into
valuable
spirocyclic-1,2-amidoalcohol
highlighting
synthetic
utility
our
methodology.
RSC Advances,
Год журнала:
2025,
Номер
15(14), С. 10634 - 10638
Опубликована: Янв. 1, 2025
The
transition-metal-free
regioselective
[3
+
2]
annulation
of
azadienes
with
haloalcohols
for
the
preparation
highly
functionalized
spiro-oxazolidines
is
experimentally
simple,
broad
substrate
scope,
good
yields,
and
excellent
regioselectivity.
An
aminocatalytic
asymmetric
(4
+
4)
annulation
of
ynones
and
unsaturated
pyrazolones
is
reported.
This
study
the
first
to
describe
an
enantioselective
synthesis
eight-membered
ether-embedded
4,5-fused
pyrazoles.
The
scope
reaction
broad,
cyclic
ether-containing
pyrazole
products
were
isolated
in
moderate
good
yields
with
high
enantioselectivities.
The
enantioselective
synthesis
of
carbazoles
and
pyrroloindolines
has
been
achieved
through
organo-catalyzed
metal
sequential-catalyzed
one-pot
reactions
indolyl
ynones.
Chiral
can
be
synthesized
from
the
ynones
nitroolefins
an
Michael
addition
followed
by
a
gold-catalyzed
Friedel-Crafts
reaction/aromatization
process.
N-tosyl
imines
lead
to
generation
via
Mannich
reaction
silver-catalyzed
dearomatizing
spirocyclization/N,N-acetalization
cascade
reaction.
