Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(51), P. 9130 - 9135
Published: Dec. 19, 2023
Herein,
we
describe
a
Brønsted-acid-catalyzed
enantioselective
desymmetrization
of
1,3-diols
with
alkynes
through
hydroalkoxylation/hydrolysis
process.
The
reaction
leads
to
the
atom-economical
synthesis
valuable
chiral
β-amino
alcohols
under
mild
conditions.
Further
synthetic
transformations
based
on
alcohol
moiety
provide
divergent
approaches
toward
N-containing
heterocycles.
Angewandte Chemie International Edition,
Journal Year:
2023,
Volume and Issue:
62(23)
Published: March 30, 2023
Axially
chiral
biaryls
widely
exist
in
natural
products
and
pharmaceuticals
are
used
as
ligands
catalysts
asymmetric
synthesis.
Compared
to
the
well-established
axially
6-membered
biaryl
skeletons,
examples
of
5-membered
have
been
quite
scarce,
mono-substituted
3-arylpyrrole
atropisomers
not
reported.
Here,
we
disclose
a
copper-catalyzed
atroposelective
diyne
cyclization
for
construction
range
arylpyrrole
good
excellent
yields
with
generally
enantioselectivities
via
oxidation
X-H
insertion
vinyl
cations.
Importantly,
this
protocol
only
represents
first
synthesis
atropisomers,
but
also
constitutes
example
atropisomer
Theoretical
calculations
further
support
mechanism
cation-involved
elucidate
origin
enantioselectivity.
Chemical Society Reviews,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 1, 2025
This
review
summarizes
the
latest
trends
and
developments
of
isoxazole-enabled
alkyne
amination
reactions
their
applications
in
divergent
heterocycle
synthesis.
Chemical Science,
Journal Year:
2023,
Volume and Issue:
14(22), P. 5918 - 5924
Published: Jan. 1, 2023
Catalytic
enantioselective
transformation
of
alkynes
has
become
a
powerful
tool
for
the
synthesis
axially
chiral
molecules.
Most
these
atroposelective
reactions
rely
on
transition-metal
catalysis,
and
organocatalytic
approaches
are
largely
limited
to
special
which
act
as
precursors
Michael
acceptors.
Herein,
we
disclose
an
intramolecular
(4
+
2)
annulation
enals
with
ynamides.
This
method
allows
efficient
highly
atom-economical
preparation
various
7-aryl
indolines
in
generally
moderate
good
yields
excellent
enantioselectivities.
Computational
studies
were
carried
out
elucidate
origins
regioselectivity
enantioselectivity.
Furthermore,
phosphine
ligand
derived
from
synthesized
indoline
was
proven
be
potentially
applicable
asymmetric
catalysis.
Green Chemistry,
Journal Year:
2023,
Volume and Issue:
25(22), P. 9092 - 9096
Published: Jan. 1, 2023
An
efficient
iron-catalyzed
sulfur
alkylation
of
sulfenamides
with
diazo
compounds
for
the
synthesis
functionalized
sulfilimines
is
developed
under
air
conditions.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(12), P. 2063 - 2067
Published: March 20, 2023
A
novel
copper-catalyzed
tandem
cyclization/direct
C(sp2)–H
annulation
of
phenyl
azide–ynamides
via
α-imino
copper
carbenes
has
been
developed,
which
provides
a
concise
and
flexible
approach
for
the
construction
range
valuable
azepino[2,3-b:4,5-b′]diindoles
in
mostly
good
to
excellent
yields
with
high
chemoselectivities.
This
reaction
also
exhibits
broad
substrate
scope,
functional
group
tolerance,
simple
operation,
mild
conditions.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: March 26, 2025
The
[2,3]-sigmatropic
rearrangement
has
been
widely
utilized
to
construct
C-S
bonds.
Herein,
we
report
an
enantioselective,
intermolecular,
and
noncarbenoid
of
sulfonium
ylides
using
azoalkenes.
This
process
features
a
broad
substrate
scope,
high
efficiency,
excellent
enantioselectivity,
achieving
yields
up
99%
enantiomeric
excess
(ee)
96%.
Furthermore,
the
protocol
demonstrated
good
scalability.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 14, 2025
Catalytic
annulation
of
isoxazoles
with
alkynes
is
an
efficient
methodology
for
the
assembly
N-heterocyclic
architectures,
and
most
reactions
require
noble-metal
catalysts.
Herein,
we
disclose
a
copper-catalyzed
formal
[4
+
1]
1,6-diynes
atom-economical
construction
biologically
important
pyrrolo[3,4-b]indoles
in
high
yields
via
vinyl
cation
intermediates,
which
significantly
different
from
previous
annulations
involving
α-imino
metal
carbene
intermediates.
Interestingly,
preliminary
results
have
been
obtained
related
catalytic
atroposelective
transformation.
Computational
mechanistic
studies
are
employed
to
elucidate
reaction
mechanism.
ACS Catalysis,
Journal Year:
2023,
Volume and Issue:
13(13), P. 8803 - 8812
Published: June 19, 2023
Herein,
an
organocatalytic
enantioselective
desymmetrizing
hydroalkoxylation
of
1,4-
and
1,8-diynes
is
disclosed,
which
represents
a
unique
chiral
Brønsted
acid-catalyzed
desymmetrization
diynes.
This
protocol
provides
facile
practical
access
to
enantioenriched
1,3-diaminopropanol
derivatives
γ-butyrolactones
with
wide
substrate
scope
generally
high
enantioselectivities.
Besides,
the
backbones
these
products
constitute
structural
core
numerous
bioactive
molecules,
they
can
serve
as
valuable
precursors
for
expeditious
assembly
versatile
N-
O-heterocycles.
Moreover,
control
experiments
theoretical
calculations
are
employed
confirm
mechanistic
rationale
elucidate
origin
enantioinduction.
Chemistry - A European Journal,
Journal Year:
2023,
Volume and Issue:
29(70)
Published: Sept. 28, 2023
Abstract
Gold
catalysis
is
an
important
method
for
alkyne
functionalization.
Here
we
report
the
gold‐catalyzed
formal
[3+2]
aminative
cyclization
of
yndiamides
and
isoxazoles
in
a
direct
synthesis
polysubstituted
diaminopyrroles,
which
are
motifs
drug
discovery.
Key
to
this
process
formation,
subsequent
cyclization,
α‐imino
gold
Fischer
carbene,
represents
new
type
carbene
intermediate.
The
reaction
proceeds
rapidly
under
mild
conditions,
with
high
regioselectivity
being
achieved
by
introducing
subtle
steric
bias
between
nitrogen
substituents
on
yndiamide.
DFT
calculations
revealed
that
key
was
interconversion
isomeric
keteniminiun
ions
via
low‐barrier
π‐complex
transition
state,
establishes
Curtin‐Hammett
scenario
isoxazole
addition.
By
using
benzisoxazoles
as
substrates,
outcome
could
be
switched
[5+2]
leading
1,4‐oxazepines.
