Journal of the American Chemical Society,
Год журнала:
2023,
Номер
145(51), С. 28085 - 28095
Опубликована: Ноя. 30, 2023
The
creation
of
full
stereoisomers
an
organic
compound
comprising
multiple
contiguous
stereocenters
with
simultaneous
control
over
both
relative
and
absolute
configurations
remains
a
significant
challenge
in
synthetic
chemistry.
Using
cooperative
catalysis
strategy,
we
established
N-heterocyclic
carbene/nickel-catalyzed
enantio-
diastereodivergent
propargylation
reaction
to
access
3,3'-disubstituted
oxindoles,
enabling
the
incorporation
internal
alkyne
functionality
introduction
single
quaternary
or
vicinal
quaternary/tertiary
stereogenic
center.
By
selecting
appropriate
combination
catalyst
chirality,
all
four
potential
α-quaternary
propargylated
oxindoles
were
synthesized
predictable
precise
way
remarkable
yields,
diastereoselectivities,
enantioselectivities
from
identical
starting
materials.
utility
this
method
was
demonstrated
concise
asymmetric
total
synthesis
(-)-debromoflustramine
B
(-)-C(β-Me)-debromoflustramine
B.
Journal of the American Chemical Society,
Год журнала:
2018,
Номер
140(39), С. 12364 - 12368
Опубликована: Сен. 20, 2018
A
Ni-catalyzed
enantioselective
reductive
diarylation
of
activated
alkenes
by
domino
cyclizative/cross-coupling
two
aryl
bromides
is
developed.
This
reaction
proceeds
under
very
mild
conditions
and
shows
broad
substrate
scope,
without
requiring
the
use
preformed
organometallic
reagents.
Moreover,
this
approach
provides
direct
access
to
various
bis-heterocycles
bearing
all-carbon
quaternary
centers
in
synthetically
useful
yields
(up
81%)
with
excellent
enantioselectivity
(>30
examples,
90–99%
ee).
ACS Catalysis,
Год журнала:
2019,
Номер
9(3), С. 1820 - 1882
Опубликована: Янв. 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.
Angewandte Chemie International Edition,
Год журнала:
2019,
Номер
58(35), С. 12190 - 12194
Опубликована: Июнь 28, 2019
Highly
enantioselective
[3+3]
and
[3+4]
annulations
of
isatin-derived
enals
with
ethynylethylene
carbonates
ethynyl
benzoxazinanones
are
enabled
by
NHC/cooper
cooperative
catalysis,
leading
to
a
big
library
spirooxindole
derivatives
in
high
structural
diversity
enantioselectivity
(up
99
%
ee).
Both
reactions
represent
nicely
synergistic
integration
NHC
copper
which
both
catalysts
activate
the
substrates
chiral
perfectly
controls
stereochemistry.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(15), С. 4315 - 4348
Опубликована: Янв. 1, 2021
Catalytic
asymmetric
MCCRs
for
enantioselective
synthesis
of
spirooxindoles
by
using
chiral
phosphoric
acids,
amines,
bifunctional
thiourea/squaramides
and
metal-based
reagents
as
catalysts.
Chemical Science,
Год журнала:
2020,
Номер
11(35), С. 9341 - 9365
Опубликована: Янв. 1, 2020
This
review
summarizes
the
advances
in
catalytic
enantioselective
construction
of
vicinal
quaternary
carbon
stereocenters,
introduces
major
synthetic
strategies
and
discusses
their
advantages
limitations,
outlines
opportunities.
Organic Letters,
Год журнала:
2019,
Номер
21(4), С. 1237 - 1240
Опубликована: Фев. 7, 2019
The
catalyst-free
electrochemical
di-
and
trifluoromethylation/cyclization
of
N-substituted
acrylamides
was
realized
under
external
oxidant-free
conditions.
strategy
provides
expedient
access
to
fluoroalkylated
oxindoles
3,4-dihydroquinolin-2(1
H)-ones
with
ample
scope
broad
functional
group
tolerance
by
mild,
direct
electrolysis
sodium
sulfinates
in
an
undivided
cell.
Detailed
mechanistic
studies
provided
strong
support
for
a
SET-based
reaction
manifold.
ACS Catalysis,
Год журнала:
2019,
Номер
10(2), С. 955 - 993
Опубликована: Дек. 11, 2019
Optically
active
α-arylation
carbonyl
units
are
widely
present
in
a
wide
variety
of
drugs,
bioactive
natural
products,
and
valuable
pharmacologically
molecules.
Catalytic
enantioselective
enolates
or
the
related
precursors
with
various
arylating
agents
constitutes
powerful
tactic
for
constructing
such
privileged
scaffolds,
which
is
great
interest
has
gained
considerable
progress.
This
review
summarizes
advances
based
on
two
major
strategies
diverse
agents,
discusses
detail
reaction
mechanism,
limitations,
advantages
each
method
their
applications,
expounds
synthetic
opportunities
still
open
further
exploration.
Chemical Communications,
Год журнала:
2019,
Номер
55(91), С. 13638 - 13648
Опубликована: Янв. 1, 2019
The
judicious
incorporation
of
a
fluoroalkyl
moiety
often
brings
about
beneficial
effects
on
the
properties
bioactive
molecules.
Consequently,
efficient
methods
for
selective
fluoroalkylation
are
much
sought
after
in
drug
discovery.
Despite
significant
achievements
trifluoromethylation,
mono-
and
difluoroalkylation
is
still
undeveloped.
Catalytic
functionalization
fluorinated
silyl
enol
ethers
(FSEEs)
emerges
as
fruitful
approach
diversity-oriented
synthesis
value-added
α-mono
or
difluoroalkylated
ketones.
In
this
feature
article,
we
detail
our
efforts
developing
catalytic
reactions
using
FSEEs.
Specifically,
highlight
findings
such
activating
FSEEs
by
amines
enantioselective
synthesis,
taking
advantage
observed
high
activity
over
non-fluorinated
analogues
reaction
development,
influence
C-FH-X
interactions
reactivity
selectivity.
Organic Letters,
Год журнала:
2019,
Номер
21(12), С. 4859 - 4863
Опубликована: Июнь 13, 2019
A
Pd-catalyzed
formal
[5
+
3]
intermolecular
cycloaddition
reaction
of
isatin-derived
α-(trifluoromethyl)imines
with
aryl
substituted
vinylethylene
carbonates
(VECs)
has
been
reported,
affording
trifluoromethyl-group-containing
spirooxindoles
fused
an
eight-membered
ring
as
a
single
diastereoisomer
in
good
yields
the
presence
Brønsted
acid
one-pot
manner
under
mild
conditions.
The
asymmetric
version
this
also
realized
using
chiral
phosphine
ligand
along
further
transformation
obtained
product
to
give
spirooxindolo
pyrrolidine
derivative
upon
oxidation.
Chemistry - An Asian Journal,
Год журнала:
2020,
Номер
15(8), С. 1225 - 1233
Опубликована: Фев. 27, 2020
The
spirooxindole
unit
is
one
of
the
most
widely
investigated
compound
skeletons
existing
in
numerous
natural
and
pharmaceutical
molecules.
Thus,
a
large
number
synthetic
methodologies
have
already
been
reported
to
construct
such
core
structure.
trifluoromethyl
group
another
privileged
organic
chemistry.
introduction
CF3
an
framework
can
significantly
improve
properties
molecule.
In
this
context,
efficient
approach
for
construction
trifluoromethyl-containing
spirooxindoles
becomes
promising
research
direction
among
communities
industry
academia.
Minireview,
recent
advances
summarized
discussed.
addition,
representative
corresponding
reaction
mechanisms
described
as
well.
