Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(16), С. 4047 - 4053
Опубликована: Июнь 30, 2021
Abstract
An
organocatalyzed
asymmetric
dearomative
[3+2]
annulation
reaction
of
electron‐deficient
2‐nitrobenzo
heteroarenes
including
2‐nitrobenzofurans,
2‐nitrobenzothiophenes
and
2‐nitroindoles
with
3‐isothiocyanato
oxindoles
was
developed.
With
a
multiple
hydrogen‐bonding
bifunctional
thiourea
as
the
catalyst,
displays
broad
substrate
scope
provides
an
access
to
structurally
diverse
polycyclic
spirooxindoles
containing
three
contiguous
stereogenic
centers
in
high
yields
good
diastereo‐
enantioselectivities
(up
99%
yield,
94:6
dr,
97%
ee).
This
organocatalysis
protocol
is
able
afford
products
complementarily
diastereoselectivity
versus
previous
work
transition
metal
catalysis.
magnified
image
Triggered
by
the
reaction
of
an
oxime
ether
with
a
rhodium
carbenoid,
nitrogen-containing
three-dimensional
frameworks
were
constructed
from
linear
motifs
via
intramolecular
cycloaddition
endo-cyclic
azomethine
ylide.
In
this
transformation,
successive
stereocenters
containing
quaternary
carbons
formed,
affording
corresponding
tricyclic
compounds
in
moderate-to-good
yields.
The
utility
these
products
was
demonstrated
through
several
transformations.
Chinese Journal of Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 20, 2025
Comprehensive
Summary
The
asymmetric
cycloaddition
reactions
of
1,3‐fused
cyclic
azomethine
ylides
have
been
extensively
studied,
but
the
non‐cyclic
α
‐functionalization
these
compounds
remains
unexplored.
Herein,
an
efficient
combination
catalytic
enantioselective
and
remote‐controlled
desymmetrization
N
‐arylmaleimides
cyclopentene‐1,3‐diones
has
achieved
with
a
catalyst
system
consisting
chiral
P,N
‐ferrocene
ligand
AgNO
2
.
This
reaction
allowed
for
synthesis
series
enantioenriched
3,4‐dihydroisoquinoline
derivatives
bearing
multiple
stereogenic
elements/centers
good
yields
stereoselectivities.
practicality
this
method
was
demonstrated
by
gram‐scale
derivatizations
products.
Organic Chemistry Frontiers,
Год журнала:
2021,
Номер
8(10), С. 2268 - 2273
Опубликована: Янв. 1, 2021
Enantioselective
[3
+
2]
annulation
of
3-hydroxymaleimides
with
quinone
monoimines
provided
a
large
variety
succinimide
fused
indolines
in
moderate
to
good
yields
enantioselectivities.
Advanced Synthesis & Catalysis,
Год журнала:
2021,
Номер
363(16), С. 4047 - 4053
Опубликована: Июнь 30, 2021
Abstract
An
organocatalyzed
asymmetric
dearomative
[3+2]
annulation
reaction
of
electron‐deficient
2‐nitrobenzo
heteroarenes
including
2‐nitrobenzofurans,
2‐nitrobenzothiophenes
and
2‐nitroindoles
with
3‐isothiocyanato
oxindoles
was
developed.
With
a
multiple
hydrogen‐bonding
bifunctional
thiourea
as
the
catalyst,
displays
broad
substrate
scope
provides
an
access
to
structurally
diverse
polycyclic
spirooxindoles
containing
three
contiguous
stereogenic
centers
in
high
yields
good
diastereo‐
enantioselectivities
(up
99%
yield,
94:6
dr,
97%
ee).
This
organocatalysis
protocol
is
able
afford
products
complementarily
diastereoselectivity
versus
previous
work
transition
metal
catalysis.
magnified
image
