Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 13, 2024
Abstract
The
synthesis
of
bicyclic
scaffolds
has
garnered
considerable
interest
in
drug
discovery
because
their
ability
to
mimic
benzene
bioisosteres.
Herein,
we
introduce
a
new
approach
that
utilizes
Lewis
acid
(Sc(OTf)
3
)‐catalyzed
σ‐bond
cross‐exchange
reaction
between
the
C−C
bond
bicyclobutanes
and
C−N
diaziridines
produce
multifunctionalized
medicinally
interesting
azabicyclo[3.1.1]heptane
derivatives.
proceeds
well
with
different
broad
range
aryl‐
as
alkenyl‐,
but
also
alkyl‐substituted
(up
98
%
yield).
Conducting
scale‐up
experiment
exploring
synthetic
transformations
cycloadducts
emphasized
practical
application
synthesis.
Furthermore,
zinc‐based
chiral
catalytic
system
was
developed
for
enantioselective
version
this
96
ee
).
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(11), P. 8930 - 8938
Published: May 28, 2024
With
electronically
unbiased
styrenes
and
indenes
as
dienophiles,
a
highly
enantioselective
all-carbon-based
inverse-electron-demand
Diels–Alder
reaction
of
electron-deficient
2-pyrones
is
reported.
Using
C1-symmetric
imidazolidine-pyrroloimidazolone
pyridine
the
tridentate
ligand
Ni(OTf)2
Lewis
acid,
diverse
bridged
bicyclic
lactones
were
obtained
in
high
yields
(88–97%
yields),
diastereoselectivities
(>95:5
dr),
enantioselectivities
(90–99%
ee).
Cyclic
enamine
2,3-dihydrofuran
also
suitable
dienophiles.
DFT
calculations
supported
concerted
[4
+
2]
cycloaddition
mechanism
for
Ni(II)
complex-catalyzed
with
enantioselectivity
caused
by
steric
factors.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(5), P. 1314 - 1321
Published: Jan. 1, 2024
A
new
class
of
chiral
bipyridine-2NO
ligands,
which
incorporate
the
advantages
both
bipyridine
skeleton
and
pyrroloimidazolone-based
N
-oxide
moiety,
was
developed.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Nov. 13, 2024
Abstract
The
synthesis
of
bicyclic
scaffolds
has
garnered
considerable
interest
in
drug
discovery
because
their
ability
to
mimic
benzene
bioisosteres.
Herein,
we
introduce
a
new
approach
that
utilizes
Lewis
acid
(Sc(OTf)
3
)‐catalyzed
σ‐bond
cross‐exchange
reaction
between
the
C−C
bond
bicyclobutanes
and
C−N
diaziridines
produce
multifunctionalized
medicinally
interesting
azabicyclo[3.1.1]heptane
derivatives.
proceeds
well
with
different
broad
range
aryl‐
as
alkenyl‐,
but
also
alkyl‐substituted
(up
98
%
yield).
Conducting
scale‐up
experiment
exploring
synthetic
transformations
cycloadducts
emphasized
practical
application
synthesis.
Furthermore,
zinc‐based
chiral
catalytic
system
was
developed
for
enantioselective
version
this
96
ee
).
New Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
48(4), P. 1688 - 1695
Published: Jan. 1, 2024
This
work
diversified
the
Py-2NO
ligand
library
recently
developed
by
our
group
and
further
expanded
application
of
chiral
ligands
in
asymmetric
catalysis.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(6), P. 1817 - 1823
Published: Jan. 1, 2024
Donor–acceptor
aminocyclopropanes
bearing
both
amino
and
carboxyl
groups
underwent
catalytic
asymmetric
ring-opening
reactions
with
diverse
oxygen
nucleophiles
to
afford
chiral
γ-oxygen-substituted
γ-aminobutyric
acid
derivatives
good
results.
Chinese Journal of Chemistry,
Journal Year:
2024,
Volume and Issue:
42(13), P. 1474 - 1480
Published: March 1, 2024
Comprehensive
Summary
The
privileged
C
2
‐symmetric
rigid
phenol‐type
ligand
is
more
attractive
but
challenging
in
asymmetric
catalysis.
Herein,
we
designed
and
synthesized
a
class
of
rigid‐featured
chiral
tridentate
Phenol‐2NO
ligands,
that
incorporate
the
advantages
both
phenol
skeleton
pyrroloimidazolone‐based
N
‐oxide
moiety,
from
readily
available
L
‐prolinamides
operationally
simple
two
steps
up
to
44%
overall
yield.
More
importantly,
using
an
achiral
quinoline
derivative
as
additive,
newly
developed
could
serve
anioic
upon
deprotonative
activation
coordinate
Zn(II)
form
highly
enantioselective
catalyst
for
Michael‐type
Friedel‐Crafts
alkylation
reaction
indoles
with
2,3‐dioxopyrrolidines.
Excellent
yields
(up
90%)
high
enantioselectivities
99%
ee)
are
obtained
wide
range
substrates
under
mild
conditions.
Experiments
DFT
calculations
revealed
mechanism
origins
enantioselectivity.
This
also
represented
first
ligand/metal
complex
by
organic
base
additive
Chemical Science,
Journal Year:
2024,
Volume and Issue:
15(46), P. 19488 - 19495
Published: Jan. 1, 2024
We
present
the
first
enantioselective
dearomative
(3+3)
cycloadditions
of
bicyclobutanes
(BCBs)
utilizing
a
chiral
Lewis
acid
catalyst
and
bidentate
chelating
BCB
substrates.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(14), P. 3188 - 3193
Published: May 29, 2024
Abstract
With
phenacyl
chlorides
as
simple
nucleophilic
species,
the
asymmetric
Darzens
reaction
of
isatins
using
Ni(acac)
2
Lewis
acid
and
imidazolidine‐pyrroloimidazolone
pyridine
ligand
is
reported.
In
presence
1
mol%
catalyst,
diverse
spiro‐epoxyoxindoles
with
two
new
contiguous
stereocenters
were
afforded
in
82–99%
yields,
>20:1
dr,
91–99%
ee.
Chiral
could
undergo
ring‐opening
reactions
further
transformations.
The
developed
method
was
applied
to
derivatization
complex
molecules
including
indomethacin,
gemfibrozil,
febuxostat‐derived
α
‐chloroketones.
A
strong
positive
nonlinear
effect
observed,
which
caused
by
precipitation
a
less‐soluble
racemic
catalyst
complex.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(14), P. 4007 - 4013
Published: Jan. 1, 2024
An
asymmetric
Michael–alkylation
reaction
with
a
reversal
of
enantioselectivity
catalyzed
by
chiral
cobalt
complexes
is
reported,
giving
spiro-cyclopropane-oxindoles
complete
and
controlled
switch
in
stereoselectivity
(up
to
99%
−98%
ee).
