The Journal of Organic Chemistry,
Journal Year:
2019,
Volume and Issue:
84(9), P. 5099 - 5108
Published: April 12, 2019
Both
the
3-fluorooxindole
and
cyclic
sulfamidate
frameworks
are
important
in
medicinal
chemistry
owing
to
their
associated
biological
activities.
We
report
an
approach
accessing
3-fully
substituted
3-fluorooxindoles,
containing
a
benzo-fused
subunit
through
highly
enantioselective
Mannich-type
reactions
between
3-fluorooxindoles
N-sulfamidate
aldimines.
These
promoted
by
commercially
available
cinchona
alkaloid
catalyst,
accommodate
broad
substrate
scope,
deliver
desired
products
yield
of
up
99%
with
enantiomeric
excess
94%.
A
plausible
reaction
pathway
is
also
presented.
Angewandte Chemie International Edition,
Journal Year:
2019,
Volume and Issue:
59(1), P. 442 - 448
Published: Oct. 26, 2019
Abstract
The
aromatic
nitrogen
atoms
of
heteroarylaldehydes
are
activated
by
carbene
catalysts
to
react
with
ketone
electrophiles.
Multi‐functionalized
cyclic
N,O‐acetal
products
afforded
in
good
excellent
yields
and
optical
purities.
Our
reaction
involves
the
formation
an
unprecedented
aza‐fulvene‐type
acylazolium
intermediate.
A
broad
range
N‐heteroaromatic
aldehydes
electron‐deficient
substrates
works
effectively
this
transformation.
Several
chiral
through
protocol
exhibit
antibacterial
activities
against
Ralstonia
solanacearum
(
Rs
)
valuable
development
novel
agrichemicals
for
plant
protection.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(14), P. 5452 - 5456
Published: June 28, 2019
Organocatalytic
asymmetric
dearomatization
of
3-nitroindoles
and
3-nitrobenzothiophenes
by
reaction
with
ethyl
4-mercapto-2-butenoate
has
been
developed.
A
range
chiral
tetrahydrothiopheneindolines
tetrahydrothiophenebenzothiophenes
bearing
three
contiguous
stereocenters
are
obtained
in
high
yields
good
diastereoselectivities
excellent
enantioselectivities.
This
is
the
first
example
thiol-triggered
catalytic
3-nitrobenzothiophenes.
Angewandte Chemie,
Journal Year:
2019,
Volume and Issue:
131(50), P. 18237 - 18242
Published: Oct. 6, 2019
Abstract
Dearomatization
of
indoles
provides
efficient
synthetic
routes
for
substituted
indolines.
In
most
cases,
serve
as
nucleophiles.
Reported
here
is
an
asymmetric
dearomatization
reaction
indole
derivatives
that
function
electrophiles.
The
combination
a
photocatalyst
and
chiral
phosphoric
acid
open
to
air
unlocks
the
umpolung
reactivity
indoles,
enabling
their
with
N
‐hydroxycarbamates
A
variety
fused
indolines
bearing
intriguing
oxy‐amines
were
constructed
in
excellent
yields
moderate
high
enantioselectivities.
Mechanistic
studies
show
realization
two
sequential
single‐electron
transfer
oxidations
key,
generating
configurationally
biased
carbocation
species
while
providing
source
stereochemical
induction.
These
results
not
only
provide
synthesis
enantioenriched
indoline
derivatives,
but
also
offer
novel
strategy
further
designing
reactions.
Chemical Communications,
Journal Year:
2019,
Volume and Issue:
55(9), P. 1283 - 1286
Published: Jan. 1, 2019
Under
cooperative
catalysis
of
iridium
and
a
Brønsted
acid,
different
C4-substituted
azlactones
react
with
vinyl
benzoxazinones
via
formal
[4+2]
cycloaddition
or
substitution
reaction
in
chemo-
stereoselective
mode.
The Journal of Organic Chemistry,
Journal Year:
2019,
Volume and Issue:
84(9), P. 5099 - 5108
Published: April 12, 2019
Both
the
3-fluorooxindole
and
cyclic
sulfamidate
frameworks
are
important
in
medicinal
chemistry
owing
to
their
associated
biological
activities.
We
report
an
approach
accessing
3-fully
substituted
3-fluorooxindoles,
containing
a
benzo-fused
subunit
through
highly
enantioselective
Mannich-type
reactions
between
3-fluorooxindoles
N-sulfamidate
aldimines.
These
promoted
by
commercially
available
cinchona
alkaloid
catalyst,
accommodate
broad
substrate
scope,
deliver
desired
products
yield
of
up
99%
with
enantiomeric
excess
94%.
A
plausible
reaction
pathway
is
also
presented.
