ChemSusChem,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 23, 2024
Abstract
Spirocyclobutyl
oxindoles,
characterized
by
their
unique
three‐dimensional
structures,
are
valuable
building
blocks
for
many
pharmacophores
and
drug
units.
However,
stereoselective
synthetic
strategies
these
scaffolds
remain
underdeveloped,
with
most
existing
methods
relying
on
transition
metal
catalysts
stoichiometric
redox
reagents.
In
this
work,
we
introduce
an
electrochemical
strain‐release
driven
cascade
spirocyclization
of
bicyclo[1.1.0]butane
(BCB)
derivatives
the
synthesis
functionalized
spirocyclobutyl
oxindoles.
Tetrabutylammonium
bromide
serves
a
dual
purpose
as
both
supporting
electrolyte
brominating
agent.
The
method
offers
broad
substrate
scope,
high
atom
economy,
excellent
diastereoselectivity.
stereoselectivity
product
is
controlled
minimizing
dipolar
repulsion
between
amide
C=O
C−Br
bonds.
We
also
explored
methodology′s
versatility
applying
it
to
various
functionalizations
demonstrated
its
scalability
practical
use.
efficient
derivatization
products
allowed
rapid
creation
diverse
library
Synlett,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 15, 2024
Abstract
Spirocyclobutanes
have
gained
significant
attention
in
medicinal
chemistry
discovery
programs
due
to
their
broad
spectrum
of
biological
activities
and
clinical
applications.
Utilizing
ring
strain
small
molecules
drive
organic
transformations
is
one
the
most
powerful
tools
chemical
synthesis.
Our
research
group
has
focused
on
developing
new
synthetic
strategies
enabled
by
construct
complex
selectively
efficiently.
This
account
summarizes
our
recent
efforts
toward
synthesis
a
library
functionalized
spirocyclobutanes
harnessing
bicyclo[1.1.0]butanes.
Three
spicrocyclization
cascades
been
developed
incorporate
diverse
range
radical
precursors
into
spirocycobutanes.
1
Introduction
2
Synthesis
Spirocyclobutyl
Lactones
-Lactams
using
Bifunctional
Reagents
3
Dual
Photoredox/Nickel
Catalysis
for
Lactams
4
Oxindoles
under
Photoredox
5
DFT
Studies
6
Conclusion
ChemSusChem,
Journal Year:
2024,
Volume and Issue:
unknown
Published: Oct. 23, 2024
Abstract
Spirocyclobutyl
oxindoles,
characterized
by
their
unique
three‐dimensional
structures,
are
valuable
building
blocks
for
many
pharmacophores
and
drug
units.
However,
stereoselective
synthetic
strategies
these
scaffolds
remain
underdeveloped,
with
most
existing
methods
relying
on
transition
metal
catalysts
stoichiometric
redox
reagents.
In
this
work,
we
introduce
an
electrochemical
strain‐release
driven
cascade
spirocyclization
of
bicyclo[1.1.0]butane
(BCB)
derivatives
the
synthesis
functionalized
spirocyclobutyl
oxindoles.
Tetrabutylammonium
bromide
serves
a
dual
purpose
as
both
supporting
electrolyte
brominating
agent.
The
method
offers
broad
substrate
scope,
high
atom
economy,
excellent
diastereoselectivity.
stereoselectivity
product
is
controlled
minimizing
dipolar
repulsion
between
amide
C=O
C−Br
bonds.
We
also
explored
methodology′s
versatility
applying
it
to
various
functionalizations
demonstrated
its
scalability
practical
use.
efficient
derivatization
products
allowed
rapid
creation
diverse
library
