Abstract
A
variety
of
structurally
diverse
spirocyclohexane
oxindoles
featuring
a
quaternary
carbon
centre
have
been
successfully
constructed
through
an
N‐heterocyclic
carbene‐catalyzed
[4+2]
annulation
isatin‐derived
enals
with
α
‐cyano‐
β
‐methylenones.
This
domino
process
exhibits
wide
substrate
tolerance,
operates
under
mild
conditions,
and
yields
products
high
enantioselectivities.
Advanced Synthesis & Catalysis,
Journal Year:
2023,
Volume and Issue:
365(24), P. 4412 - 4439
Published: Nov. 16, 2023
Abstract
Spirooxindoles
are
privileged
scaffolds
in
diverse
bioactive
natural
products
and
pharmaceuticals,
significant
achievements
for
the
construction
of
these
molecules
have
thus
been
made
past
years.
Among
them,
organocatalysis,
particular,
nucleophilic
Lewis
base
catalysis,
has
recently
emerged
as
an
efficient
reliable
method
preparation
valuable
functionalized
spirooxindoles.
According
to
different
kinds
catalysts,
we
summarize
classify
three
catalytic
strategies;
tertiary
amine‐catalyzed
cycloadditions,
NHC‐catalyzed
phosphine‐catalyzed
respectively.
Through
methods,
potential
spirooxindole
skeletons
owning
various
functional
groups
can
be
produced
enrich
small
organic
molecule
library.
In
this
review,
describe
a
comprehensive
updated
advances
cycloaddition
reactions
Meanwhile,
related
mechanism
application
annulation
strategies
product
total
synthesis
will
highlighted
detail.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
22(1), P. 37 - 54
Published: Nov. 27, 2023
Developing
efficient
and
straightforward
strategies
to
rapidly
construct
structurally
distinct
diverse
organic
molecules
is
one
of
the
most
fundamental
tasks
in
synthesis,
drug
discovery
materials
science.
In
recent
years,
divergent
synthesis
functional
from
same
starting
has
attracted
significant
attention
been
recognized
as
an
powerful
strategy.
To
achieve
this
objective,
proper
adjustment
reaction
conditions,
such
catalysts,
solvents,
ligands,
etc.,
required.
review,
we
summarized
efforts
chemo-,
regio-
stereodivergent
reactions
involving
acyclic
cyclic
systems
catalyzed
by
palladium
complexes.
Meanwhile,
types,
including
carbonylative
reactions,
coupling
cycloaddition
well
probable
mechanism
have
also
highlighted
detail.
Advanced Science,
Journal Year:
2024,
Volume and Issue:
11(31)
Published: June 17, 2024
Abstract
Oxazocines
are
key
structural
intermediates
in
the
synthesis
of
natural
products
and
pharmaceutical
molecules.
However,
oxazocines
especially
a
highly
enantioselective
manner,
is
long‐standing
formidable
challenge
due
to
unfavorable
energetics
involved
cyclization.
Herein,
series
new
PNP‐Ligand
P
‐chiral
stereocenter
first
designed
synthesized,
called
MQ‐Phos
,
successfully
applied
it
Pd‐catalyzed
higher‐order
formal
[4+4]‐cycloaddition
α
β
‐unsaturated
imines
with
2‐(hydroxymethyl)‐1‐arylallyl
carbonates.
The
reaction
features
mild
conditions,
excellent
regio‐
enantiocontrol
broad
substrate
scope
(54
examples).
Various
medium‐sized
rings
can
be
afforded
moderate
yields
(up
92%)
enantioselectivity
99%
ee).
newly
developed
critical
for
ring
catalytic
reactivity
enantioselectivity.
Catalysts,
Journal Year:
2024,
Volume and Issue:
14(4), P. 219 - 219
Published: March 22, 2024
In
the
past
few
decades,
N-heterocyclic
carbenes
(NHCs)
have
opened
new
field
of
organocatalysis
in
synthetic
organic
chemistry.
This
review
highlights
dramatic
progress
NHC-catalyzed
C–O
bond
formation
based
on
activation
aldehyde
C(sp2)–H
bonds.
The
oxidative
and
redox
transformations
for
synthesis
various
molecules
with
structural
diversity
complexity
are
summarized.
Furthermore,
methods
strategies
NHC
catalysis
emerging
continuously;
thus,
cooperative
Brønsted
acid,
hydrogen-bonding
catalyst,
transition-metal
photocatalyst
also
described.
Chemical Communications,
Journal Year:
2024,
Volume and Issue:
60(70), P. 9400 - 9403
Published: Jan. 1, 2024
A
refined
strategy
has
been
developed
to
control
the
regioselective
asymmetric
(4+3)
cyclization
of
α-(3-isoindolinonyl)
propargylic
alcohols
with
2-indolylmethanols,
utilizing
chiral
phosphoric
acid
catalysis.
This
innovative
organocatalytic
yields
spiro
isoindolinone-oxepine-fused
indoles
featuring
a
spiro-quaternary
stereocenter
in
high
and
enantioselectivities,
facilitated
by
solvent
1,1-dichloro-1-fluoroethane
additive
hexafluoroisopropanol.
Additionally,
photophysical
properties
product
3k
are
examined,
revealing
bright
fluorescence
both
solution
solid
state.
Catalysts,
Journal Year:
2024,
Volume and Issue:
14(8), P. 508 - 508
Published: Aug. 6, 2024
We
reported
palladium-catalyzed
regioselective
[3+2]
cycloadditions
of
α,β-unsaturated
imines
with
vinylethylene
carbonates,
providing
the
desired
oxazolidines
in
moderate-to-high
yields.
This
reaction
provides
a
facile
route
for
highly
synthesis
functional
oxazolidines.
The
synthetic
utility
current
method
was
also
demonstrated
by
gram-scale
reaction.
