Chemical Science,
Journal Year:
2017,
Volume and Issue:
8(9), P. 6645 - 6649
Published: Jan. 1, 2017
An
enantioselective
hydroxylative
dearomatization
of
2-naphthols
with
oxaziridines
has
been
accomplished
using
a
N,N'-dioxide-scandium(iii)
complex
catalyst.
Various
substituted
ortho-quinols
could
be
obtained
in
high
yields
(up
to
99%)
and
enantioselectivities
95
:
5
er).
This
methodology
applied
the
synthesis
bioactive
lacinilenes
gram-scale
reaction.
Based
on
experimental
investigations
previous
work,
possible
catalytic
model
was
proposed.
Chemical Reviews,
Journal Year:
2018,
Volume and Issue:
119(3), P. 1855 - 1969
Published: Dec. 24, 2018
In
this
review,
we
summarize
the
origin
and
advancements
of
iridium-catalyzed
asymmetric
allylic
substitution
reactions
during
past
two
decades.
Since
first
report
in
1997,
Ir-catalyzed
have
attracted
intense
attention
due
to
their
exceptionally
high
regio-
enantioselectivities.
been
significantly
developed
recent
years
many
respects,
including
ligand
development,
mechanistic
understanding,
substrate
scope,
application
synthesis
complex
functional
molecules.
an
explicit
outline
ligands,
mechanism,
scope
nucleophiles,
applications
is
presented.
ACS Central Science,
Journal Year:
2021,
Volume and Issue:
7(3), P. 432 - 444
Published: Feb. 22, 2021
Asymmetric
catalysis
has
been
recognized
as
the
most
enabling
strategy
for
accessing
chiral
molecules
in
enantioenriched
forms.
Catalytic
asymmetric
dearomatization
is
an
emerging
and
dynamic
research
subject
catalysis,
which
received
considerable
attention
recent
years.
The
direct
transformations
from
readily
available
aromatic
feedstocks
to
structurally
diverse
three-dimensional
polycyclic
make
catalytic
reactions
of
broad
interest
both
organic
synthesis
medicinal
chemistry.
However,
inherent
difficulty
disruption
aromaticity
demands
a
large
energy
input
during
process,
might
be
incompatible
with
conditions
generally
required
by
catalysis.
In
this
Outlook,
we
will
discuss
representative
strategies
examples
various
compounds
try
convince
readers
that
overcoming
above
obstacles,
could
advance
chemical
sciences
many
respects.
ACS Catalysis,
Journal Year:
2019,
Volume and Issue:
9(3), P. 1820 - 1882
Published: Jan. 31, 2019
The
catalytic
enantioselective
assembly
of
spirocyclic
molecules
featuring
a
spiro
quaternary
carbon
stereocenter
is
currently
great
interest
because
such
privileged
3D
structures
are
widely
present
in
natural
products
that
exhibit
broad
spectrum
biological
and
pharmacological
activities.
This
review
summarizes
the
advances
based
on
six
major
synthetic
strategies
showcases
reaction
mechanisms
detail.
advantages
limitations
each
strategy
presented,
remaining
opportunities
outlined.
Journal of the American Chemical Society,
Journal Year:
2017,
Volume and Issue:
139(30), P. 10188 - 10191
Published: July 17, 2017
We
report
asymmetric
dearomatization
of
phenols
using
Ag
carbenoids
from
α-diazoacetamides.
The
catalyst
promoted
intramolecular
phenols,
whereas
a
Rh
or
Cu
caused
C-H
insertion
and
Büchner
reaction.
Studies
indicated
have
carbocation-like
character,
making
their
behavior
properties
unique.
Highly
enantioselective
transformations
not
been
reported.
achieved
carbenoid-mediated
chemo-
highly
phenol
with
substrate
generality
for
the
first
time.
Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
56(45), P. 14257 - 14261
Published: Sept. 20, 2017
Abstract
A
novel
palladium‐catalyzed
three‐component
reaction
of
phenol‐derived
biaryls
with
N‐benzoyloxyamines
and
norbornadiene
(NBD)
has
been
developed
for
the
assembly
highly
functionalized
spiroindenes.
This
domino
process
was
realized
through
NBD‐assisted
C−H
amination
phenol
dearomatization
by
forming
one
C−N
bond
two
C−C
bonds
in
a
single
step.
Preliminary
studies
indicated
that
asymmetric
control
this
transformation
feasible
chiral
ligands.
Moreover,
potential
synthetic
utility
methodology
highlighted
series
further
transformations.
Angewandte Chemie International Edition,
Journal Year:
2017,
Volume and Issue:
56(10), P. 2767 - 2771
Published: Jan. 27, 2017
A
novel
palladium(0)-catalyzed
dearomatizing
[2+2+1]
spiroannulation
of
1-bromo-2-naphthols
with
aryl
iodides
and
alkynes
was
developed
for
the
rapid
assembly
spiro[indene-1,1'-naphthalen]-2'-ones.
This
three-component
cascade
reaction
realized
through
consecutive
Catellani-type
C-H
activation,
unsymmetrical
biaryl
coupling,
alkyne
migratory
insertion,
arene
dearomatization.
The
potential
utility
our
method
is
illustrated
by
one-step
construction
polycyclic
skeletons
dalesconols
B
from
alkyne-tethered
1-bromo-2-naphthol.
Journal of the American Chemical Society,
Journal Year:
2016,
Volume and Issue:
138(16), P. 5234 - 5237
Published: April 7, 2016
A
catalytic,
enantioselective
γ-alkylation
of
α,β-unsaturated
malonates
and
ketoesters
is
reported.
This
strategy
entails
a
highly
regio-
iridium-catalyzed
α-alkylation
an
extended
enolate,
subsequent
translocation
chirality
to
the
γ-position
via
Cope
rearrangement.
Angewandte Chemie International Edition,
Journal Year:
2016,
Volume and Issue:
55(45), P. 14111 - 14115
Published: Oct. 10, 2016
Abstract
A
highly
enantioselective
dearomative
[3+2]
cycloaddition
of
benzothiazole
has
been
successfully
developed.
wide
range
benzothiazoles
and
cyclopropane‐1,1‐dicarboxylates
are
suitable
substrates
for
this
reaction.
The
desired
hydropyrrolo[2,1‐b]thiazole
compounds
were
obtained
in
excellent
enantioselectivity
yields
(up
to
97
%
ee
yield).
With
the
same
catalytic
system,
a
efficient
kinetic
resolution
2‐substituted
was
also
realized.
