Organic & Biomolecular Chemistry,
Journal Year:
2018,
Volume and Issue:
16(33), P. 6025 - 6034
Published: Jan. 1, 2018
An
efficient
three-component
one-pot
[3
+
2]
cycloaddition
of
isatins,
1,2,3,4-tetrahydroisoquinolines
and
methyleneindolinones
has
been
developed.
This
reaction
proceeded
in
a
highly
diastereoselective
manner
to
afford
wide
range
pyrrolo[1,2-a]isoquinoline-based
bispirooxindoles
up
91%
yields.
Additionally,
gram-scale
experiment
some
chemical
transformations
were
conducted.
ACS Catalysis,
Journal Year:
2019,
Volume and Issue:
9(5), P. 3906 - 3912
Published: March 26, 2019
Herein,
we
developed
a
copper-catalyzed
O-vinylation
of
arylhydroxylamine
using
vinyliodonium
salts
as
vinylation
reagents
to
generate
transient
O-vinyl-N-arylhydroxylamine
that
rapidly
undergoes
[3,3]-sigmatropic
rearrangement
and
subsequent
cyclization/rearomatization
form
substituted
indole.
A
wide
range
highly
indoles
benzoindoles
can
be
afforded
in
good
yields.
This
approach
is
readily
scalable,
the
scope
application
this
process
are
presented.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(13), P. 5068 - 5073
Published: May 27, 2020
Reported
herein
is
an
unprecedented
multicomponent
one-pot
dearomative
multifunctionalization
of
commercially
available
azaarenes
through
in
situ
activation
strategy,
which
not
only
achieved
the
first
full
exploitation
reactive
sites
azaarenes,
but
also
accomplished
efficient
synthesis
bridged
hydrogenated
pyridines
and
(iso)quinolines
a
highly
regioselective
diastereoselective
manner.
In
addition,
we
could
successfully
realize
step-controlled
trifunctionalization
bifunctionalization
quinolines.
Organic & Biomolecular Chemistry,
Journal Year:
2021,
Volume and Issue:
19(35), P. 7544 - 7574
Published: Jan. 1, 2021
This
review
focuses
on
recent
developments
in
the
synthesis
of
pyrrolo[1,2-
a
]indole
derivatives.
The
mechanism,
factors
affecting
yield
and
selectivity
product,
application
to
bioactive
molecules
are
explained.
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
Organic Letters,
Journal Year:
2018,
Volume and Issue:
20(3), P. 804 - 807
Published: Jan. 22, 2018
A
previously
unreported
activation
mode
is
developed
through
the
generation
of
dearomatizative
tetraenamine
species
between
5-allylic
furfurals
and
a
bifunctional
amine-thiourea
catalyst.
The
very
remote
ζ,η-alkenes
perform
as
effective
HOMO-raised
dienophiles
in
inverse-electron-demand
oxa-Diels–Alder
cycloadditions
with
isatin-derived
oxadiene
substrates,
delivering
multifunctional
spirocyclic
oxindoles
incorporating
dihydropyran
skeleton
moderate
to
high
yields
good
excellent
enantio-
diastereoselectivity.
Organic Letters,
Journal Year:
2019,
Volume and Issue:
21(2), P. 481 - 485
Published: Jan. 10, 2019
An
efficient
one-pot
synthesis
of
polysubstituted
pyrrolizines
from
N-vinyl-α,β-unsaturated
nitrones
and
activated
alkynes
through
iron(III)/copper(II)-cocatalyzed
[3
+
2]
cycloaddition/[3,3]-rearrangement
sequential
N–O
bond
cleavage
was
developed.
The
reaction
first
underwent
cycloaddition
[3,3]-rearrangement
to
afford
nine-membered
N-heterocycles,
then
a
controlled
rings
by
iron(III)/copper(II)
cocatalysts
delivered
pyrrolizine
scaffolds.
A
kinetic
resolution
ring
compounds
achieved
for
the
time
using
copper(II)
acetate
combined
with
chiral
PyBox
ligand.
Organic & Biomolecular Chemistry,
Journal Year:
2019,
Volume and Issue:
17(47), P. 10020 - 10029
Published: Jan. 1, 2019
A
simple
and
efficient
visible-light-catalyzed
cascade
sulfonylation/cyclization
of
N-propargylindoles
with
K2S2O5
aryldiazonium
tetrafluoroborates
for
the
construction
2-sulfonyl-substituted
9H-pyrrolo[1,2-a]indoles
is
developed.
Organic Letters,
Journal Year:
2020,
Volume and Issue:
22(3), P. 873 - 878
Published: Jan. 9, 2020
New
chalcone-based
pyridinium
salts
have
been
successfully
exploited,
which
could
smoothly
participate
in
the
highly
diastereoselective
dearomatization
with
binucleophilic
enaminones
by
taking
advantage
of
their
multiple
reactive
sites
to
construct
bibridged
benzoazepines
up
89%
yields.
The
key
success
was
skillful
and
unprecedented
C-3
functionalization
new
salts.
This
work
not
only
provides
a
kind
novel
salt
synthon
but
also
achieves
first
complex
challenging
high
synthetic
efficiency.
