Molecules,
Journal Year:
2023,
Volume and Issue:
28(23), P. 7898 - 7898
Published: Dec. 1, 2023
α-Substituted-7-azaindoline
amides
and
α,β-unsaturated
7-azaindoline
have
emerged
as
new
versatile
synthons
for
various
metal-catalyzed
organic-catalyzed
asymmetric
reactions,
which
attracted
much
attention
from
chemists.
In
this
review,
the
progress
of
research
on
in
aldol
reaction,
Mannich
conjugate
addition,
1,3-dipole
cycloaddition,
Michael/aldol
cascade
aminomethylation
Michael
addition-initiated
ring-closure
reaction
is
discussed.
The
α-substituted-7-azaindoline
amides,
nucleophiles,
are
classified
according
to
type
α-substituted
group,
whereas
electrophiles,
reaction.
ACS Catalysis,
Journal Year:
2024,
Volume and Issue:
14(12), P. 9254 - 9264
Published: June 3, 2024
Catalytic
asymmetric
dearomatization
reactions
of
α-unsubstituted
β-naphthols
are
very
challenging
due
to
the
high
energy
barrier
resulting
from
loss
aromaticity.
Herein,
we
describe
an
example
enantioselective
catalytic
dearomative
spiroannulation
with
yne-allylic
esters.
The
success
this
reaction
relied
on
copper-catalyzed
remote
strategy
using
esters
as
bis-electrophilic
reagents.
This
transformation
features
mild
conditions,
broad
functional
group
tolerance,
and
extensive
substrate
scope,
thereby
facilitating
efficient
construction
array
enantioenriched
naphthalene-2-one
spiroindolenine
derivatives.
Experimental
studies
density
theory
calculations
establish
pathway
origin
stereoselectivity.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(13), P. 2623 - 2628
Published: March 24, 2024
An
efficient
dearomative
cyclization
of
2-nitrobenzofurans
via
a
thiol-triggered
tandem
Michael
addition/intramolecular
Henry
reaction
has
been
developed.
A
range
thiochromeno[3,2-b]benzofuran-11-ols
and
tetrahydrothieno[3,2-b]benzofuran-3-ols
could
be
obtained
in
up
to
99%
yield
>20:1
dr.
The
valuable
thiochromone
fused
benzofurans
prepared
with
the
2-mercaptobenzaldehyde
reaction/rearomatization/oxidative
dehydrogenation
process
one-pot
two-step
operation.
mechanism
for
was
tentatively
proposed.
Organic Chemistry Frontiers,
Journal Year:
2023,
Volume and Issue:
10(13), P. 3401 - 3428
Published: Jan. 1, 2023
This
review
summarizes
the
advances
in
field
of
intramolecular
kinetic
resolution
(KR)
mediated
by
non-enzymatic
catalysts.
The
relative
classification
KR
is
accomplished
and
several
categories
reactions
are
discussed.
Chemical Communications,
Journal Year:
2023,
Volume and Issue:
59(24), P. 3590 - 3593
Published: Jan. 1, 2023
An
asymmetric
allylic
dearomatization
reaction
of
1-nitro-2-naphthol
derivatives
with
Morita-Baylis-Hillman
(MBH)
adducts
has
been
developed.
By
utilizing
Pd
catalyst
derived
from
Pd(OAc)2
and
Trost
ligand
(R,R)-L1,
the
proceeded
smoothly
in
1,4-dioxane
at
room
temperature,
affording
substituted
β-naphthalenones
good
yields
(up
to
92%)
enantioselectivity
90%
ee).
A
range
1-nitro-2-naphthols
MBH
were
found
be
compatible
under
optimized
conditions.
This
provides
a
convenient
method
for
synthesis
enantioenriched
1-nitro-β-naphthalenone
derivatives.
Journal of the American Chemical Society,
Journal Year:
2022,
Volume and Issue:
145(1), P. 610 - 625
Published: Dec. 20, 2022
Enantioselective
[2
+
2]
cyclization
between
an
imine
and
a
carbon–carbon
double
bond
is
versatile
strategy
to
build
chiral
azetidines.
However,
α-branched
allenoates
have
never
been
successfully
applied
in
reactions
with
imines,
as
they
always
undergo
Kwon's
[4
annulation
previous
catalytic
methods.
Herein,
simple
situ
generated
magnesium
catalyst
was
employed
achieve
the
enantioselective
reaction
of
DPP-imines
for
first
time.
Insightful
experiments
including
KIE
experiments,
controlled
Hammett
plot
analysis,
31P
NMR
studies
initial
intermediates
indicate
that
current
most
likely
involves
asynchronous
concerted
transition
state.
Further
mechanistic
investigations
by
combining
kinetic
studies,
ESI
coordination
complexes,
on
rates
under
different
loading
amounts
provided
details
this
allenoates.
This
new
approach
synthesis
various
aza-heterocycles,
key
intermediate
lipid-lowering
agent
Ezetimibe.
Organic Chemistry Frontiers,
Journal Year:
2022,
Volume and Issue:
9(23), P. 6586 - 6591
Published: Jan. 1, 2022
An
electrochemical
dearomative
spirocyclization
in
flow
has
been
developed,
featuring
the
use
of
electrons
as
clean
oxidant
a
minimum
amount
electrolytes
to
afford
diverse
spirodienones
short
reaction
time.
Advanced Synthesis & Catalysis,
Journal Year:
2024,
Volume and Issue:
366(6), P. 1412 - 1421
Published: Jan. 23, 2024
Abstract
We
demonstrate
the
application
of
chiral
magnesium
complexes
in
an
asymmetric
carbon‐sulfur
bond‐forming
reaction.
Enantioselective
and
cost‐effective
methodology
under
mild
condition
for
thia‐Michael
addition,
utilizing
situ
generated
dinuclear
magnesium‐ProPhenol
complex,
has
been
developed.
The
versatility
this
protocol
is
demonstrated
with
a
broad
range
thiol
nucleophiles
wide
selection
enones.
Enantioenriched
β‐ketosulfides
are
obtained
good
to
excellent
yields
moderate
enantioselectivity.
presented
catalytic
system
exhibits
tolerance
structurally
different
substrates
while
maintaining
high
This
observation
aligns
proposed
mechanism,
wherein
sulfur
atom
coordinates
catalyst
close
proximity
reaction
center.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(24), P. 4778 - 4800
Published: Jan. 1, 2024
A
review
is
presented
of
magnesium
catalysis
for
the
synthesis
important
chiral
scaffolds.
Several
motifs
that
are
present
in
classic
ligands
or
natural
products
synthesized
by
Mg(
ii
)
catalytic
methods
briefly
discussed.
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(5), P. 867 - 871
Published: Feb. 1, 2023
By
development
of
ProPhenol/Ti(IV)
catalysts,
a
catalytic
enantioselective
hydroxylative
dearomatization
naphthols
is
achieved
by
using
TBHP
as
simple
oxidative
reagent.
The
side
coordinative
chain
equipped
on
the
C1-position
β-naphthols
plays
an
important
role
for
initiating
this
asymmetric
reaction,
which
might
be
result
proper
cocoordination
effects
to
titanium
center
in
catalyst.
A
reasonable
cycle
proposed,
system
applied
range
type
phenolic
compound,
and
related
concise
transformations
are
carried
out.
Synlett,
Journal Year:
2023,
Volume and Issue:
35(10), P. 1089 - 1100
Published: Nov. 10, 2023
Abstract
This
Account
summarizes
the
highly
appealing
dearomatization
reactions
of
β-naphthols
for
synthesis
functionalized,
three-dimensional
structures
starting
with
simple
planar
aromatic
compounds.
The
are
categorized
mainly
from
viewpoint
construction
carbon–hydrogen,
carbon–carbon,
and
carbon–hetero
bonds
(C–N/O,
C–Cl,
C–F)
at
α-position
β-naphthols.
dearomatized
products
play
an
important
role
in
organic
materials
science.
1
Introduction
2
Construction
Carbon–Hydrogen
Bonds
α-Position
β-Naphthols
3
Carbon–Carbon
4
Carbon–Nitrogen/Oxygen
Double
Bond
5
Carbon–Oxygen
6
Carbon–Halogen
7
Conclusion
