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.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(16), P. 2125 - 2136
Published: Jan. 1, 2024
In
this
feature
article,
we
focus
on
the
photochemical
strategy
for
construction
of
heterocyclic
skeletons,
specifically
highlighting
methods
that
employ
visible
light-promoted
carbene
transfer
reactions.
ACS Catalysis,
Journal Year:
2025,
Volume and Issue:
unknown, P. 5796 - 5805
Published: March 25, 2025
The
transition
metal-catalyzed
asymmetric
[n
+
2]
cycloaddition
reaction
with
oxy-substituted
ketene
intermediates
remains
a
synthetic
challenge
due
to
the
limited
availability
of
suitable
precursors.
Herein,
we
report
visible-light-driven,
palladium-catalyzed
[4
vinyl
benzoxazinanones
siloxyketene
intermediates,
generating
structurally
diverse
chiral
quinolinone
derivatives
satisfactory
diastereo-
and
enantioselectivities.
transient
generation
siloxyketenes
from
α-ketoacylsilylanes
through
visible-light-induced
Brook
rearrangement
is
important
for
success
present
cycloaddition.
13C-labeling
experiments
reveal
pathway
involving
[1,3]-silyl
migration
process.
side
arm
effects
BOX
ligand
silyl
steric
hindrance
α-ketoacylsilanes
play
crucial
roles
in
stereoselectivity
control,
theoretical
calculations
provide
insights
into
stereochemical
outcome
reaction.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(4), P. 1034 - 1041
Published: Jan. 1, 2023
A
series
of
dihydroquinolinones
have
been
synthesized
via
synergistic
catalysis
combining
photolysis
and
Lewis
base
utilizing
in
situ
generated
ketenes
ortho
-amino
MBH
carbonates.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(11), P. 3250 - 3256
Published: Jan. 1, 2024
An
unusual
visible-light-induced
[1,3]-brook
rearrangement
of
α-ketoacylsilanes
for
cascade
cyclization
with
1,3,5-triazinanes
and
C
,
N
-cyclic
azomethine
imines
has
been
realized
to
assemble
various
β-lactams
pyrazolidinone
scaffolds.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: April 17, 2025
Compared
to
smaller
or
larger
rings,
seven-
and
eight-membered
carbo-
heterocycles
are
typically
nonplanar
exhibit
greater
conformational
rigidity.
This
property
alone
can
impart
chirality
certain
7-
8-membered
ring
systems.
Herein,
we
summarize
recent
achievements
in
the
enantioselective
synthesis
of
this
class
inherently
chiral
medium
including
both
construction
modification,
as
well
applications
ligands
catalysts
derived
from
these
rigid
cyclic
scaffolds
asymmetric
catalysis.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(18), P. 4474 - 4487
Published: Jan. 1, 2023
Photogenerated
ketenes
simplify
and
accelerate
the
synthesis
of
diverse
cyclic
architectures
demonstrate
their
promising
applications
in
flow
chemistry.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(18), P. 4698 - 4702
Published: Jan. 1, 2023
A
novel
asymmetric
[4
+
4]
dipolar
cycloaddition
of
aliphatic
1,4-dipoles
with
azadienes
was
developed
to
construct
chiral
benzofuran-
and
indene-fused
eight-membered
N-heterocycles
in
good
yields
excellent
stereoselectivities.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(10), P. 2864 - 2869
Published: Jan. 1, 2024
A
novel
palladium-catalyzed
[4
+
4]
cycloaddition
of
2-pyrones
with
2-alkylidenetrimethylene
carbonates
has
been
developed
for
the
synthesis
bridged
eight-membered
oxygen
heterocycles
in
good
yields
and
excellent
stereoselectivities.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(10), P. 2911 - 2916
Published: Jan. 1, 2024
The
challenging
8-membered
lactone
derivatives
bearing
two
vicinal
chiral
stereocenters
were
synthesized
via
a
cascade
reaction
mediated
by
the
squaramide.
