Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(6), P. 1154 - 1159
Published: Feb. 7, 2024
The
direct
functionalization
of
β-C(sp2)-H
bonds
in
enamides
has
garnered
increasing
attention
within
the
realm
organic
synthesis.
However,
these
remarkable
advancements
are
predominantly
dependent
on
transition
metals;
limited
success
been
achieved
via
organocatalytic
catalysis.
Herein,
we
report
a
CPA-catalyzed
cascade
intramolecular
cyclization
to
synthesize
chiral
dihydropyrimido[1,6-a]indoles
bearing
gem-difluoromethylene.
Moreover,
this
methodology
enables
synthesis
diverse
with
outstanding
enantioselectivities
moderate
high
yields.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(21), P. 5421 - 5427
Published: Jan. 1, 2023
A
class
of
ketimines
was
first
prepared
and
used
in
an
asymmetric
aza-Friedel–Crafts
reaction
for
the
highly
enantioselective
synthesis
tryptanthrin
derivatives.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(5), P. 1430 - 1436
Published: Jan. 1, 2024
Herein,
the
synthesis
of
2-(3,3-difluoro-2-phenylindolin-2-yl)-1-phenylethan-1-one
scaffolds
through
asymmetric
Mannich
reactions
between
3,3-difluoro
cyclic
ketimines
and
simple
ketones
is
described.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(39), P. 5902 - 5905
Published: Jan. 1, 2023
The
chiral
phosphoric
acid-catalyzed
asymmetric
intermolecular
formal
[3+2]
cycloaddition
of
azoalkenes
with
azlactones
has
been
established.
This
convergent
protocol
leads
to
a
facile
and
enantioselective
de
novo
construction
wide
range
fully
substituted
4-pyrrolin-2-ones
bearing
carbon
atom
in
good
yields
excellent
enantioselectivities
(26
examples,
72-95%
87-99%
ee).
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.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Jan. 25, 2025
The
synthesis
of
chiral
gem-difluorinated
spiro-heterocyclic
compounds
continues
to
be
a
significant
challenge
in
organic
chemistry
due
their
widespread
applications
across
various
fields.
Therefore,
efficient
asymmetric
approaches
for
the
spiroindanone-dihydroquinazolinones
are
particularly
valuable,
especially
industrial
manufacturing
fluorinated
drugs.
Herein,
we
developed
CPA-catalyzed
enantioselective
cyclization
reactions
gem-difluoroalkyl
1,3-indandiones
with
anthranilamides
achieve
2,2-difluoro-spiroindanone-dihydroquinazolinones
good
high
yields
excellent
enantioselectivities.
Moreover,
mechanism
experiment
proved
that
gem-difluoro
substitution
pattern
promotes
reaction.
Chinese Journal of Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 19, 2025
Comprehensive
Summary
The
demands
for
effective
assembly
of
structurally
complex
molecular
scaffolds
from
simple
starting
materials
are
continuously
growing
along
with
the
development
organic
chemistry.
We
have
developed
a
tandem
approach
that
assembles
β
‐chloroethylphosphane,
alkynyl
imines
(or
ketones),
and
nitrones
into
isoxazolidine
fused
phospholene
through
sequential
process
involving
phospha‐Michael
addition,
intramolecular
cyclization,
dearomatizing
[3+2]
cycloaddition
reactions.
isoxazolidine‐fused
has
three
heteroatoms,
including
junction
phosphorus
atom.
After
removing
coordinated
tungsten
group,
these
compounds
can
serve
as
potential
P‐stereogenic
ligands
may
biological
activities.
Contrary
to
pyrroles
furans,
aromatic
2‐phosphapyrroles
2‐phosphafurans
good
2π‐electron
candidates
in
dearomative
reactions
due
poor
overlap
2p‐3p
orbitals
C=P
moiety.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 20, 2025
A
palladium-catalyzed
three-component
1,3-dienylation
of
propargylic
esters
with
DABSO
and
aryl
iodides
has
been
developed.
This
novel
reductive
cross-coupling
reaction
produces
2-sufonylated
1,3-dienes
as
single
products
in
the
presence
metal
Mn
high
regio-
chemoselectivities.
Control
experiments
demonstrated
that
transformation
may
undergo
a
radical
process.
Organic Letters,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 22, 2025
The
enantioselective
formal
(3
+
2)
cyclization
and
sequential
reaction
of
2-malononitrile-substituted
oxindoles
with
benzaldehydes
ortho-aminobenzaldehydes
were
achieved
by
chiral
N,N′-dioxide/metal
complex
Lewis
acid
catalysts.
This
protocol
supplies
facile
efficient
access
to
highly
functionalized
dihydrofuran-
azepine-based
spirooxindoles.
Based
on
the
control
experiments
deuterium
labeling
studies,
interconversion
diastereomeric
intermediates
under
conditions
reversible
1,5-H
transfer
step
disclosed.
