Angewandte Chemie,
Journal Year:
2020,
Volume and Issue:
133(17), P. 9276 - 9288
Published: July 28, 2020
Abstract
Due
to
the
synergistic
“push–pull”
effect
of
vicinal
electron‐donating
and
electron‐withdrawing
groups,
donor–acceptor
(D‐A)
cyclopropanes
have
been
recognized
as
one
most
powerful
building
blocks
generate
polyfunctional
reactive
intermediates
after
a
strain‐driven
ring
cleavage.
Enantioselective
reactions
D‐A
provide
an
efficient
approach
enantioenriched
acyclic
cyclic
compounds.
A
number
chiral
Lewis/Brønsted
acids,
transition
metals,
organocatalysts
designed
for
such
transformations,
including
ring‐openings,
annulations,
rearrangements.
This
minireview
highlights
developments
new
advances
in
this
field
describes
synthetic
opportunities
offered
by
these
interesting
methodologies.
Chemical Reviews,
Journal Year:
2020,
Volume and Issue:
121(1), P. 227 - 263
Published: May 29, 2020
This
review
describes
the
development
of
enantioselective
methods
for
ring
opening
cyclopropanes.
Both
approaches
based
on
reaction
nonchiral
cyclopropanes
and
(dynamic)
kinetic
resolutions
asymmetric
transformations
chiral
substrates
are
presented.
The
is
organized
according
to
substrate
classes,
starting
by
more
mature
field
donor-acceptor
Emerging
acceptor-
or
donor-only
then
last
part
reactive
three-membered
rings
substituted
with
unsaturations
a
particular
focus
vinylcyclopropanes,
alkylidenecyclopropanes,
vinylidenecyclopropanes.
In
two
decades,
has
grown
from
proof
concept
stage
broad
range
accessing
enantioenriched
building
blocks,
further
extensive
developments
can
be
expected
in
future.
Chemical Reviews,
Journal Year:
2020,
Volume and Issue:
121(1), P. 110 - 139
Published: Aug. 6, 2020
In
this
review,
transition
metal-catalyzed
methodologies
and
applications
that
exploit
C–C
bond
cleavage
of
vinylcyclopropanes
(VCPs)
are
summarized
with
a
focus
on
cycloaddition
related
addition
reactions.
Transition
metals,
including
palladium,
nickel,
iron,
ruthenium,
rhodium,
cobalt,
iridium,
can
catalyze
the
bonds
in
activated
or
nonactivated
VCPs.
Additionally,
these
bond-breaking
reactions
occur
as
intra-
intermolecular
processes.
The
properties
VCPs
discussed
Introduction.
Various
involving
then
next
chapter.
cycloadditions
following
Finally,
challenges
potential
opportunities
outlined
last
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
60(17), P. 9192 - 9204
Published: July 28, 2020
Due
to
the
synergistic
"push-pull"
effect
of
vicinal
electron-donating
and
electron-withdrawing
groups,
donor-acceptor
(D-A)
cyclopropanes
have
been
recognized
as
one
most
powerful
building
blocks
generate
polyfunctional
reactive
intermediates
after
a
strain-driven
ring
cleavage.
Enantioselective
reactions
D-A
provide
an
efficient
approach
enantioenriched
acyclic
cyclic
compounds.
A
number
chiral
Lewis/Brønsted
acids,
transition
metals,
organocatalysts
designed
for
such
transformations,
including
ring-openings,
annulations,
rearrangements.
This
minireview
highlights
developments
new
advances
in
this
field
describes
synthetic
opportunities
offered
by
these
interesting
methodologies.
Chemical Society Reviews,
Journal Year:
2022,
Volume and Issue:
51(10), P. 4146 - 4174
Published: Jan. 1, 2022
The
advances
on
metal-catalysed
high-order
dipolar
annulations
were
comprehensively
summarized
in
this
review.
To
further
exploit
the
potential
of
unique
annulation
strategy,
a
research
outlook
was
also
proposed.
Journal of the American Chemical Society,
Journal Year:
2021,
Volume and Issue:
143(2), P. 1038 - 1045
Published: Jan. 6, 2021
Cycloaddition
reactions
between
oxyallyl
cations
and
alkenes
are
important
transformations
for
the
construction
of
ring
systems.
Although
(4
+
3)
cycloaddition
well-developed,
(3
2)
cycloadditions
remain
rare,
an
asymmetric
version
has
not
yet
been
developed.
Moreover,
because
highly
electrophilic,
only
electron-rich
olefins
can
be
used
as
partners.
We
herein
report
a
method
enantioselective
palladium-oxyallyl
species
electron-deficient
nitroalkenes.
This
transformation
was
enabled
by
rationally
designed
hydrogen-bond-donating
ligand
(FeUrPhos)
proceeded
via
inverse
electron
demand
pathway.
Using
this
method,
we
could
assemble
cyclopentanones
with
up
to
three
contiguous
stereocenters
high
enantioselectivity
good
excellent
diastereoselectivity.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(6), P. 2292 - 2297
Published: March 8, 2021
Ligand-controlled,
palladium-catalyzed
asymmetric
[4+4]
and
[2+4]
cycloaddition
reactions
of
benzofuran-derived
azadienes
have
been
developed.
Taking
advantage
chiral
P,N-ligand
(S,Rp)-PPFA,
we
obtained
a
variety
benzofuro[2,3-c][1,5]
oxazocines
in
good
yields
with
excellent
enantioselectivities
via
reactions.
Employing
P,P-ligand
(S)-Cl-MeO-BIPHEP,
the
chemo-
regioselectivities
were
switched
to
synthesize
tetrahydropyran-fused
spirocyclic
compounds
efficiency
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(18), P. 3960 - 3982
Published: Jan. 1, 2021
Bridged
polycycles
are
privileged
molecular
skeletons
with
wide
occurrence
in
bioactive
natural
products
and
pharmaceuticals.
Therefore,
they
have
been
the
pursing
target
molecules
of
numerous
chemists.
The
rapid
convenient
generation
sp3-rich
complex
three-dimensional
from
simple
easily
available
aromatics
has
made
dearomatization
a
highly
valuable
synthetic
tool
for
construction
rigid
challenging
bridged
rings.
This
review
summarizes
the-state-of-the-art
advances
strategies
application
ring
formation,
discusses
their
advantages
limitations
in-depth
mechanism,
highlights
value
total
synthesis
products.
We
wish
this
will
provide
an
important
reference
medicinal
chemists
inspire
further
development
intriguing
research
area.
Chemistry - A European Journal,
Journal Year:
2020,
Volume and Issue:
26(67), P. 15354 - 15377
Published: July 24, 2020
Abstract
The
efficient
and
selective
synthesis
of
functionalized
seven‐membered
rings
remains
an
important
pursuit
within
synthetic
organic
chemistry,
as
this
motif
appears
in
numerous
drug‐like
molecules
natural
products.
Use
cycloaddition
reactions
attractive
approach
for
their
construction
the
perspective
atom
step
economy.
Additionally,
ability
to
combine
multiple
components
a
single
reaction
has
potential
allow
combinatorial
strategies
diversity‐oriented
synthesis.
inherent
entropic
penalty
associated
with
achieving
these
transformations
impressively
been
overcome
development
catalysis,
whereby
can
be
pre‐organized
through
activation
by
transition‐metal‐catalysis.
fine‐tuning
metal/ligand
combinations
well
conditions
allows
chemo‐,
regio‐,
diastereo‐
enantioselectivity
transformations.
Herein,
we
discuss
recent
advances
transition‐metal‐catalyzed
via
combination
2–4
mediated
variety
metals.
An
emphasis
is
placed
on
mechanistic
aspects
both
illustrate
state
science
highlight
unique
application
novel
processes
transition‐metals
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(7), P. 2600 - 2605
Published: March 25, 2020
A
method
for
the
synthesis
of
diverse
polysubstituted
quinolines
from
readily
available
acrylic
acids
and
anthranils
has
been
developed.
The
weakly
coordinating
–COOH
directing
group,
which
can
be
tracelessly
removed
in
cascade
cyclization,
is
essential
this
reaction.
Diverse
were
obtained
under
mild
reaction
conditions
with
simple
H2O
CO2
as
byproducts.
More
importantly,
1,2,3,4-tetrahydroacridine,
core
skeleton
tacrine
(an
Alzheimer's
disease
drug),
was
conveniently
synthesized.
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
59(26), P. 10396 - 10400
Published: March 25, 2020
This
work
reports
gold-catalyzed
[4+3]-annulations
of
2-(1-alkynyl)-2-alken-1-ones
with
anthranils
to
yield
epoxybenzoazepine
products
excellent
exo-diastereoselectivity
(dr>25:1).
The
utility
this
new
gold
catalysis
is
manifested
by
applicable
substrates
over
a
broad
scope.
More
importantly,
the
enantioselective
versions
these
[4+3]-cycloadditions
have
been
developed
satisfactorily
chiral
catalysts
under
ambient
conditions
(DCM,
0
°C);
ee
levels
range
from
88.0-99.9
%.
With
DFT
calculations,
we
postulate
stepwise
pathway
rationalize
preferable
exo-stereoselection.
